4-amino-3-methylsulfanylphenol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This compound was prepared from 3-(Methylsulfanyl)4-nitrophenol (3.2 g, 17.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.18 g (81.3%) of the title compound. 1H-NMR (DMSO-d6) δ 8.56 (s, 1H), 6.60 (d, J=2.7 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.43 (dd, J=8.7, 2.4 Hz, 1H), 2.28 (s, 3H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Iron powder (1.59 g, 28.5 mmol) was added slowly to a solution of 3-(methylthio)-4-nitrophenol (1.76 g, 9.5 mmol) in acetic acid (50 mL) and ethanol (5 mL). The mixture was stirred 17 hours at room temperature.v Then iron was removed with a magnet and the slurry mixture filtered. The filtrate was diluted in water (100 mL) and neutralised with a saturated solution of Na2CO3. The mixture was extracted with DCM, and the combined organic layer dried over Na2SO4. Then, the solvent was evaporated under vacuum to provide the title compound (780 mg, 53%) as a grey powder. 1H-NMR (δ, ppm, DMSO-d6): 2.29 (s, 3H, HMe), 4.48 (bs, 2H, NH2), 6.44 (d, 1H, Harom 5, J6-5=8.5 Hz), 6.54 (d, 1H, Harom 6, J6-5=8.5 Hz), 6.61 (s, 1H, Harom 2), 8.58 (broad s, 1H, OH). GC-MS (m/z): 155.09 v Then iron was removed with a magnet the slurry mixture filtered The filtrate was diluted in water (100 mL) The mixture was extracted with DCM the combined organic layer dried over Na2SO4 Then, the solvent was evaporated under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100° C. and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100° C. stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This compound was prepared from 3-(Methylsulfanyl)4-nitrophenol (3.2 g, 17.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.18 g (81.3%) of the title compound. 1H-NMR (DMSO-d6) δ 8.56 (s, 1H), 6.60 (d, J=2.7 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.43 (dd, J=8.7, 2.4 Hz, 1H), 2.28 (s, 3H).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1). the mixture stirred for 10 more minutes the mixture was heated to 100′C stirred for 3 hours After cooling down the mixture extracted three times with EtOAc The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution water, dried over MgSO4 evaporated