Triethylsilane → 3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol

Participants

Role	Name	HCID	Charge
Reactant	Triethylsilane	HCID 12052	—
Reactant	3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-ol	HCID 14973207	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol	HCID 2438	90.5%

Reaction Steps

By a method similar to Preparation 20, using 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-hydroxy-1H-indole (1.25 g, 5.47 mmol) in dichloromethane (5 mL) trifluoroacetic acid (5 mL), triethylsilane (875 mL, 6.0 mmol) afforded 1.14 g (90%) of the title compound as a tan solid: mp=233-237° C.; 1H NMR (400 MHz, dmso-d6): 10.41 (br s, 1H), 8.52 (br s, 1H), 7.08 (d, 1H, J=8.0 Hz), 6.92 (d, 1H, J=2.0 Hz), 6.80 (d, 1H, J=2.0 Hz), 6.53 (dd, 1H, J=8.4, 2.0 Hz), 2.84 (br d, 2H, J=11.2 Hz), 2.63-2.50 (m, 1H), 2.19 (s, 3H), 2.08-1.97 (m, 2H), 1.85 (br d, 2H, J=12.0 Hz), 1.72-1.57 (m 2H); MS (ES+) m/e 231.0 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07230011B2
Source dataset	uspto-grants-2007_06
ORD ID	ord-93299e3949c547b185d8bd2dc02fde9c
Source note	uspto-grants-2007_06