Benzoyl chloride → N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide

HRID 28680

반응식

HRID 28680 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

생성물 1

HCID 11406023N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)benzamide수율 26%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine (50 mg, 0.19 mmol) and benzoyl chloride (24 μL, 0.21 mmol) in dichloromethane (1 mL) at 0° C. was added diisopropylethylamine (66 μL, 0.38 mmol). The mixture was stirred at room temperature 15 hours, the solvent removed, and the residue purified by flash chromatography (0-30% ethyl acetate-hexanes) to give 18 mg (26% yield) of a yellow solid. 1H-NMR (CDCl3): δ 8.97 (s, 1H), 7.78 (d, 2H), 7.61 (m, 1H), 7.52 (m, 1H), 7.44 (t, 2H), 7.23 (m, 1H), 7.17 (d, 1H), 6.42 (d, 1H), 5.34 (m, 1H), 2.72 (m, 2H), 2.32 (m, 1H), 2.02-1.93 (m, 3H); MS m/z 369 (M−1).

후처리

  1. customthe solvent removed
  2. customthe residue purified by flash chromatography (0-30% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-b49dcf9f9b4249aaba23456d368fe08c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419997B2

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