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

HRID 1159839Notes

Reaction equation

HRID 1159839 reaction equation
[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.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][C:23]=1[C:32]([F:35])([F:34])[F:33]>>[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([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:29])=[O:30])=[CH:24][C:23]=1[C:32]([F:35])([F:33])[F:34]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27375494-Fluoro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595135621-(1-{[4-Fluoro-3-(trifluoromethyl)phenyl]sulfonyl}-5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamineYield 10%

Procedure

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 4-fluoro-3-(trifluoromethyl)benzenesulphonyl chloride (29 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 (3 mg, 8%) as a white solid. MS (ESI+) for C19H18F4N2O3S m/z 431 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-637210515f6f4a45b81aa53c6b7b399e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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