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

HRID 1882802Notes

Reaction equation

HRID 1882802 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:15][C:14](=[O:16])[O:13][C:8]3([CH2:12][CH2:11][CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.[Cl:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[Cl:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[CH:4][C:5]3[NH:15][C:14](=[O:16])[O:13][C:8]4([CH2:12][CH2:11][CH2:10][CH2:9]4)[C:6]=3[CH:7]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 235095896-bromo-spiro-[4H-3,1-benzoxazine-4,1'-cyclopentane]-2-(1H)-one

Product 1

HCID 99013826-(3-Chlorophenyl)-spiro-[4H-3,1-benzoxazine-4,1'-cyclopentane]-2(1H)-one

Procedure

Prepared from 6-bromo-spiro-[4H-3,1-benzoxazine-4,1′-cyclopentane]-2-(1H)-one and 3-chlorophenyl boronic acid according to Procedure A. Off-white solid: mp 140-145° C. 1H-NMR (DMSO-d6) δ10.27 (s, 1H), 7.75 (t, 1H, J=1.8 Hz), 7.53-7.63 (m, 3H), 7.44 (t, 1H, J=7.9 Hz), 7.36 (m, 1H), 6.95 (d, 1H, J=8.6 Hz), 2.09-2.15 (m, 4H), 1.81-1.89 (m, 4H). MS (ESI) m/z 314 [M+H]+. Anal. Calc. For C18H16ClNO2: C, 68.90; H, 5.14; N, 4.46. Found: C, 60.94; H, 4.94; N, 3.78.

Sources & evidence

ORD record
ord-7691b5d4de854faa8c347e76dedde09f
Source dataset
uspto-grants-2004_07
Patent number
US06759408B2

Reaction notes

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