Dimethylformamide → 1-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

HRID 1159843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159843
[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.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[F:28]>>[Cl:21][C:22]1[CH:23]=[C:24]([S:29]([N:8]2[C:9]3[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)(=[O:30])=[O:31])[CH:25]=[CH:26][C:27]=1[F:28]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Produkt 1

HCID 595135471-{1-[(3-Chloro-4-fluorophenyl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamineAusbeute 14,4 %

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 3-chloro-4-fluorobenzene-1-sulfonyl chloride (25 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, 14%) as a white solid. MS (ESI+) for C18H18ClFN2O3S m/z 397 (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-52ec87b012444beba3a53b3996b07081
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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