3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 7-(3-Chloro-4-fluorophenyl)-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(H)-one

HRID 1816913Notes

Reaction equation

HRID 1816913 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:18])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:19]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[F:27]>>[CH3:18][C:7]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[O:8][CH2:9][C:10](=[O:12])[NH:11][C:5]2[CH:4]=[CH:3][C:2]([C:23]3[CH:24]=[CH:25][C:26]([F:27])=[C:21]([Cl:20])[CH:22]=3)=[CH:19][C:6]1=2

Participants

3

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 688661097-Bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 112921607-(3-Chloro-4-fluorophenyl)-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(H)-one

Procedure

Prepared from 7-bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-chloro-4-fluorobenzeneboronic acid generally according to the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.13 (s, 1H), 7.86 (dd, J=6.8, 2.0 Hz, 1H), 7.64 (m, 2H), 7.55 (m, 2H), 7.48 (t, J=8.8 Hz, 1H), 7.25 (d, J=8.3 Hz, 1H), 6.99 (dd, J=4.9, 3.4 Hz, 1H), 6.91 (dd, J=3.4, 1.0 Hz, 1H), 4.16 (d, J=16.1 Hz, 1H), 4.06 (d, J=16.1 Hz, 1H), 2.08 (s, 3H); MS (ES) m/z 388 (M+H)+; Anal. Calc. For C20H15ClFNO2S: C, 61.93, H, 3.90; N, 3.61. Found: C, 61.88, H, 3.99; N, 3.35.

Sources & evidence

ORD record
ord-4773186f7e434862bd24660c3d9b8595
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

Loading…