Dimethylformamide → HCID 59513522, compound

HRID 1159836Notes

Reaction equation

HRID 1159836 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.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>>[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:26]1[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=1)(=[O:31])=[O:30])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513522HCID 59513522, compoundYield 7.6%

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-methoxybenzene-1-sulfonyl chloride (23 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 using preparative HPLC/UV (System B) afforded the title product (2 mg, 6%) as a white solid. MS (ESI+) for C19H22N2O4S m/z 375 (M+H)+.

Workup

  1. stirringto stir at rt over night
  2. customThe reaction was quenched by addition of water
  3. customPurification

Sources & evidence

ORD record
ord-b39160532658422ab7d80ebf477a9711
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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