2-Bromophenyl methyl sulphone

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: Using compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (the product of step (b) in Example 35) (50 mg, 0.102 mmol), o-methylsulfonylbromobenzene (29 mg, 0.122 mmol), tetrakis (triphenylphosphine) palladium (12 mg, 0.010 mmol), and cesium carbonate (66 mg, 0.204 mmol) as starting materials, preparation following the method as described in Example 35 (c) afforded off-white solid 19 mg, yield: 35.2%. materials, preparation

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-bromo(methylsulfonyl)benzene (1.10 g, 4.7 mmol) and anhydrous piperazine (2.02 g, 23.5 mmol) was heated at 110° C. overnight. Then, the mixture was cooled and partitioned between 2 N NaOH and CH2Cl2. The separated organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude residue was chromatographed (CHCl3/CH3OH, 9:1, as eluent) to give 8 as a white semisolid (0.36 g, 34% yield). 1H NMR: δ 2.58 (s, 1H, NH, D2O exchanged), 2.84 (s, 4H, piperazinic), 3.14 (s, 3H, CH3), 7.10-7.83 (m, 4H, aromatic). Then, the mixture was cooled partitioned between 2 N NaOH and CH2Cl2 The separated organic layer was dried over Na2SO4 concentrated under reduced pressure The crude residue was chromatographed (CHCl3/CH3OH, 9:1, as eluent)

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

実験手順: The title compound was prepared in a manner similar to that described in Example 444 using 7-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine and 1-bromo-2-(methylsulfonyl)benzene. MS (ESI): mass calcd. for C20H17FN2O3S, 384.09; m/z found, 385.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.27-8.24 (m, 1H), 7.99-7.93 (m, 1H), 7.71-7.65 (m, 1H), 7.63-7.57 (m, 1H), 7.47 (m, 1H), 7.41-7.38 (m, 1H), 7.33-7.27 (m, 3H), 4.32-4.24 (m, 2H), 3.67-3.59 (m, 2H), 2.76 (s, 3H).

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

実験手順: Using compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (the product of step (b) in Example 35) (50 mg, 0.102 mmol), o-methylsulfonylbromobenzene (29 mg, 0.122 mmol), tetrakis (triphenylphosphine) palladium (12 mg, 0.010 mmol), and cesium carbonate (66 mg, 0.204 mmol) as starting materials, preparation following the method as described in Example 35 (c) afforded off-white solid 19 mg, yield: 35.2%. materials, preparation