(3-Cyano-5-fluorophenyl)boronic acid → HCID 11315741, compound

HRID 1816908Notes

Reaction equation

HRID 1816908 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]([CH:18]([CH3:20])[CH3:19])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:21]=1.[C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[C:28]([F:30])[CH:29]=1)#[N:23]>>[F:30][C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH:18]([CH3:20])[CH3:19])([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[C:6]=3[CH:21]=2)[CH:27]=1)[C:22]#[N:23]

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 68863750HCID 68863750, compound

Product 1

HCID 11315741HCID 11315741, compound

Procedure

Prepared from 7-bromo-5-isopropyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-cyano-5-fluorobenzeneboronic acid using the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.07 (s, 1H), 8.03 (s, 1H), 7.90 (m, 1H), 7.84 (m, 1H), 7.77 (m, 2H), 7.51 (dd, J=5.0, 1.2 Hz, 1H), 7.24 (d, J=8.5 Hz, 1H), 7.04 (m, 2H), 4.20 (d, J=14.4 Hz, 1H), 3.96 (d, J=14.4 Hz, 1H), 2.90 (m, 1H), 0.92 (t, J=6.4 Hz, 6H); MS (ES) m/z 407 (M+H)+.

Sources & evidence

ORD record
ord-aa474668139f4938ab146c8b68ef7ebe
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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