4-Hydroxypyrrolidine → (4'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-3-yl)-methanol

Participants

Role	Name	HCID	Charge
Reactant	4-Hydroxypyrrolidine	HCID 98210	—
Reactant	Piperidin-3-ylmethanol	HCID 107308	—
Reactant	2-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine	HCID 21906809	—
Product	(4'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-3-yl)-methanol	HCID 21906789	—

Reaction Steps

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with 3-hydroxymethyl piperidine. A yellow solid 115 was obtained (0.0279 g, 60%). 1H-NMR (CDCl3, 400 MHz) δ 1.32-1.42 (m, 1H), 1.63-1.74 (m, 1H), 1.86-1.95 (m, 2H), 2.04-2.14 (m, 1H), 3.18-3.25 (m, 1H), 3.33-3.39 (m, 1H), 3.47-3.52 (m, 1H), 3.71 (dd, J=4.0 Hz, 11.0 Hz, 1H), 3.83 (s, 3H), 4.02-4.07 (m, 1H), 4.48-4.53 (m, 1H), 6.93 (d, J=6.6 Hz, 1H), 7.00-7.08 (m, 4H), 7.45-7.52 (m, 3H), 7.84 (s, 1H), 8.35 (d, J=6.5 Hz, 1H); MS (APCI) m/z 475 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06787542B2
Source dataset	uspto-grants-2004_09
ORD ID	ord-bf4b47c5ea0b4ce1b7f5340a7c9e83a7
Source note	uspto-grants-2004_09