3-bromo-N,N-dimethylaniline

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反応条件: temp:120.01; pressure:0.00; stir:

実験手順: Prepared from 3-bromo-N,N-dimethylaniline (1i, 40.0 mg, 0.200 mmol, 1.00 equiv) and catBH (36.0 mg, 0.300 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3i[S4] (40.1 mg, 62%) as a white solid.

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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 from 4-methyl-5-thiazolecarbaldehyde and 3-bromo-N,N-dimethylaniline using the method of Example 32. M.p. 135°-138° C.

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

実験手順: A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, 1 mmol), (3-bromo-phenyl)-dimethyl-amine (600 mg, 3 mmol), K3PO4 (636 mg, 3 mmol), L-Proline (69 mg, 0.6 mmol) and CuI (57 mg, 0.3 mmol) in dry DMF (4 mL) was stirred at 150° C. for 16 h. The reaction mixture was cooled to RT, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by column chromatography using neutral alumina and 10% EtOAc-Hexane to yield [3-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-phenyl]-dimethyl-amine as an off white solid (11 mg). 1H NMR (Oxalate salt, CD3OD) d (ppm): 7.40 (t, 1H), 7.30 (s, 1H), 7.10 (d, 1H), 7.86 (d, 1H), 6.64 (m, 2H), 4.58 (m, 2H), 3.64 (m, 2H), 3.16 (s, 3H), 3.08 (m, 2H), 2.96 (s, 6H), 2.42 (s, 3H). extracted with EtOAc The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure to afford crude material, which was purified by column chromatography

反応条件: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of (3-bromophenyl)dimethylamine (7.5 g, 37.5 mmol) in THF (50 mL) at −78° C., was added n-butyllithium (2.88 g, 45.0 mmol). The resulting solution was stirred at −35° C. for 1 h and was then cooled to −78° C. and treated dropwise with a solution of N-methyl-N-(methyloxy)butanamide (4.92 g, 37.5 mmol) (Description 25) in dry THF (15 mL). The resulting mixture was stirred for 45 min at −78° C. and then worked up using water (100 mL) and ethyl acetate (200 mL). The crude material was purified by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in hexane, to afford the title compound (3.48 g). LCMS (B) m/z: 192 [M+1]+, Rt 2.29 min. was then cooled to −78° C. The resulting mixture was stirred for 45 min at −78° C. The crude material was purified by chromatography on silica gel eluting with a gradient of 0-20% ethyl acetate in hexane

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