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

HRID 1159849Notes

Reaction equation

HRID 1159849 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]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31]>>[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:30]([C:24]1[CH:25]=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=1[O:22][CH3:21])(=[O:32])=[O:31])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 113450482-Methoxy-4-methylbenzene-1-sulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595135581-{5-Methoxy-1-[(2-methoxy-4-methylphenyl)sulfonyl]-1H-indol-4-yl}-N,N-dimethylmethanamineYield 18.4%

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-methoxy-4-methylbenzenesulfonyl chloride (24 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 white solid. MS (ESI+) for C20H24N2O4S m/z 389 (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-94beff075cf541afad1d9cf9dc3e62c1
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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