Dimethylformamide → 2-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrile

HRID 1159845노트

반응식

HRID 1159845 반응식
[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CN(C=O)C.[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30])#[N:22]>>[CH3:15][N:13]([CH2:12][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]#[N:22])(=[O:31])=[O:30])[CH3:14]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2회

생성물 1

HCID 595135952-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrile수율 23.2%

실험 절차

To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 2-cyanobenzenesulphonyl chloride (22 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at rt over night. The reaction was quenched by addition of water. Purification by preparative HPLC/UV (System B) afforded the title product (6 mg, 22%) as a white solid. MS (ESI+) for C19H19N3O3S m/z 370 (M+H)+.

후처리

  1. stirringto stir at rt over night
  2. customThe reaction was quenched by addition of water
  3. customPurification by preparative HPLC/UV (System B)

출처 및 근거

ORD 기록
ord-81a4715d39f54e6a931a48917915366a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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