(3-Chlorophenyl)boronic acid → 6-(3-Chlorophenyl)-spiro[4H-3,1-benzoxazine-4,1'-cyclohexane]-2-(1H)-one

HRID 1634945Notes

Reaction equation

HRID 1634945 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:16][C:15](=[O:17])[O:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[CH:4][C:5]3[NH:16][C:15](=[O:17])[O:14][C:8]4([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[C:6]=3[CH:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 220219046-Bromospiro[4H-3,1-benzoxazine-4,1'-cyclohexan]-2(1H)-one

Product 1

HCID 99019436-(3-Chlorophenyl)-spiro[4H-3,1-benzoxazine-4,1'-cyclohexane]-2-(1H)-one

Procedure

Prepared according to Procedure A from 6-bromo-spiro[4H-3,1-benzoxazine-4,1′-cyclohexane]-2(1H)-one and 3-chlorophenyl boronic acid. Off-white solid: mp 165-168° C. 1H-NMR (DMSO-d6) δ10.25 (s, 1H), 7.74 (t, 1H, J=1.9 Hz), 7.50-7.67 (m, 3H), 7.42-7.49 (m, 1H), 7.35-7.38 (m 1H), 6.93-6.95 (d, 1H, J=4.2 Hz), 1.91-1.98 (m, 4H), 1.64-1.76 (m, 3H), 1.60 (m, 2H), 1.29-1.39 (m, 1H); MS (APCI) m/z 328 ([M+H]+, 80%)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-94cdd38eb16849cc8dce7937c94fbc45
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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