Dimethylformamide → 2-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrile

HRID 1159845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159845
[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:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30])#[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:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]#[N:22])(=[O:31])=[O:30])[CH3:14]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Produkt 1

HCID 595135952-({4-[(Dimethylamino)methyl]-5-methoxy-1H-indol-1-yl}sulfonyl)benzonitrileAusbeute 23,2 %

Versuchsvorschrift

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-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 (6 mg, 22%) as a white solid. MS (ESI+) for C19H19N3O3S m/z 370 (M+H)+.

Aufarbeitung

  1. stirringto stir at rt over night
  2. customThe reaction was quenched by addition of water
  3. customPurification by preparative HPLC/UV (System B)

Quellen und Nachweise

ORD-Eintrag
ord-81a4715d39f54e6a931a48917915366a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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