Tetrabutylammonium Fluoride → 3-(4-Methylpiperazin-1-YL)-1H-indole

HRID 736973Notes

Reaction equation

N1(C2C3C(=CC=CC=3)NC=2)CCOCC1.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([Si](C(C)C)(C(C)C)C(C)C)[CH:24]=2)[CH2:19][CH2:18]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:21][CH2:22]1

Participants

Reactant 3

HCID 2724141Tetrabutylammonium Fluoride

HCID 125308333-Morpholin-4-yl-1H-indole

HCID 589751093-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indole

Product 1

HCID 534146913-(4-Methylpiperazin-1-YL)-1H-indole

Procedure

Following a method similar to 3-morpholin-4-yl-1H-indole using 3-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indole (0.35 g, 0.94 mmol) and 1N solution of tetrabutylammonium fluoride (1.40 mL) to prepare the title compound. Purify by flash chromatography using 2 to 12% methanol in dichloromethane to give the title compound (0.12 g 60%). MS (ES) 216.1 (M+1)+.

Sources & evidence

ORD record: ord-1584515b0c00488caea2f74df2553798
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595339B2

Reaction notes

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