Dimethylformamide → 3-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrile

HRID 1159857Notes

Reaction equation

HRID 1159857 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.[C:21]([C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)#[N:22]>>[CH3:15][N:13]([CH2:12][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:29]([C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:21]#[N:22])(=[O:31])=[O:30])[CH3:14]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 595136163-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrileYield 15.5%

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 3-cyanobenzenesulphonyl chloride (22 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 (4 mg, 13%) as a white solid. MS (ESI+) for C19H19N3O3S m/z 370 (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-fed3683090ac428296ebf11be91c5028
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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