Dimethylformamide → HCID 59513565, Verbindung

Reaktionsgleichung

[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.[O:21]1[C:27]2[CH:28]=[CH:29][C:30]([S:32](Cl)(=[O:34])=[O:33])=[CH:31][C:26]=2[O:25][CH2:24][CH2:23][CH2:22]1>>[O:21]1[C:27]2[CH:28]=[CH:29][C:30]([S:32]([N:8]3[C:9]4[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=4)[CH:6]=[CH:7]3)(=[O:34])=[O:33])=[CH:31][C:26]=2[O:25][CH2:24][CH2:23][CH2:22]1

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 27763863,4-dihydro-2H-1,5-benzodioxepine-7-sulfonyl chloride

HCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Produkt 1

HCID 59513565HCID 59513565, VerbindungAusbeute 17,2 %

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 3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonyl chloride (27 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 yellow solid. MS (ESI+) for C21H24N2O5S m/z 417 (M+H)+.