Dimethylformamide → 1-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

HRID 1159843노트

반응식

HRID 1159843 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.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[F:28]>>[Cl:21][C:22]1[CH:23]=[C:24]([S:29]([N:8]2[C:9]3[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)(=[O:30])=[O:31])[CH:25]=[CH:26][C:27]=1[F:28]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2회

생성물 1

HCID 595135471-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine수율 14.4%

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 3-chloro-4-fluorobenzene-1-sulfonyl chloride (25 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 (4 mg, 14%) as a white solid. MS (ESI+) for C18H18ClFN2O3S m/z 397 (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-52ec87b012444beba3a53b3996b07081
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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