Dimethylformamide → 1-{1-[(2,5-Dimethoxyphenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

HRID 1159854Notes

Reaction equation

HRID 1159854 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]([O:29][CH3:30])=[CH:25][C:24]=1[S:31](Cl)(=[O:33])=[O:32]>>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[S:31]([N:8]1[C:9]2[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)(=[O:32])=[O:33]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 1370252,5-Dimethoxybenzenesulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595136051-{1-[(2,5-Dimethoxyphenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamineYield 17.7%

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 2,5-dimethoxybenzenesulfonyl chloride (26 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 beige solid. MS (ESI+) for C20H24N2O5S m/z 405 (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-8212e53cf5fa44c69dc61d0fc44d819e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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