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

HRID 1246858Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.OC1CCNC1.[OH:33][CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]1>>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:37]3[CH2:38][CH2:39][CH2:40][CH:35]([CH2:34][OH:33])[CH2:36]3)[CH:7]=2)=[CH:9][C:10]=1[C:23]([F:26])([F:25])[F:24]

Participants

Reactant 3

HCID 982104-Hydroxypyrrolidine

HCID 107308Piperidin-3-ylmethanol

HCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906789(4'-(4-(2-Methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-3-yl)-methanol

Procedure

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)+.

Sources & evidence

ORD record: ord-83d1b6d4034a41a48f27ba862f8469e3
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129247B2

Reaction notes

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