Dimethylformamide → HCID 59513620, compound

HRID 1159855Notes

Reaction equation

HRID 1159855 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]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30]>>[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([F:21])([F:33])[F:34])(=[O:31])=[O:30])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513620HCID 59513620, compoundYield 17.3%

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 2-(trifluoromethyl)benzenesulfonyl chloride (27 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 (5 mg, 17%) as a colorless solid. MS (ESI+) for C19H19F3N2O3S m/z 413 (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-31e650db5bbd4146ac3f001bafc0c12f
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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