(3-hydroxyphenyl)boronic Acid → HCID 59643903, compound

HRID 2252436Notes

Reaction equation

HRID 2252436 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[O:18])[C@@H:9]2[CH2:19][CH2:20][C@@H:21]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[OH:22])=[N:6][CH:7]=1.[OH:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C@@H:21]([OH:22])[CH2:20][CH2:19][C@@H:9]2[C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([C:35]4[CH:34]=[CH:33][CH:32]=[C:31]([OH:30])[CH:36]=4)=[CH:7][N:6]=3)[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]2=[O:18])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59643966HCID 59643966, compound

Product 1

HCID 59643903HCID 59643903, compoundYield 87%

Procedure

(3R,4S)-4-(5-Bromopyridin-2-yl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-phenylazetidin-2-one (23 mg, 0.051 mmol) was coupled with 3-hydroxyphenyl boronic acid (9.2 mg, 0.067 mmol) under standard Suzuki conditions illustrated by Example 42. Purification by chromatography (4 g silica gel, 15% to 100% ethyl acetate-hexane) afforded (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[5-(3-hydroxyphenyl)pyridin-2-yl]-1-phenylazetidin-2-one (20.7 mg, 87% yield) as a clear film; Rf 0.14 (1:1 ethyl acetate-hexane); 1H NMR (300 MHz, CDCl3) δ 8.88 (d, J=2.2 Hz, 1H), 7.88 (dd, J=8.2, 2.3 Hz, 1H), 7.86-7.80 (m, 1H), 7.39-7.22 (m, 7H), 7.12-7.02 (m, 3H), 6.96 (t, J=8.7 Hz, 2H), 6.96-6.91 (m, 1H), 4.97 (d, J=2.3 Hz, 1H), 4.76-4.72 (m, 1H), 3.28-3.22 (m, 1H), 3.20 (br s, 1H), 2.17-1.90 (m, 4H), 1.80 (br s, 1H) ppm; MS [M+H]+ 469.0.

Workup

  1. customPurification by chromatography (4 g silica gel, 15% to 100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6c6df83501304e96a3eccfe96ce3ad2d
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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