(3-Cyano-5-fluorophenyl)boronic acid → HCID 44585548, compound

HRID 2252571Notes

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]([CH2:18][CH3:19])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:20]=1.[F:21][C:22]1[CH:23]=[C:24]([C:31]#[N:32])[CH:25]=[C:26](B(O)O)[CH:27]=1>>[CH2:18]([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:26]3[CH:25]=[C:24]([CH:23]=[C:22]([F:21])[CH:27]=3)[C:31]#[N:32])=[CH:20][C:6]1=2)[CH3:19]

Participants

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acid

HCID 68863777HCID 68863777, compound

Product 1

HCID 44585548HCID 44585548, compound

Procedure

Prepared from 7-bromo-5-ethyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 5-fluoro-3-cyanobenzeneboronic acid using the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.12 (s, 1H), 8.07 (s, 1H), 7.95 (dt, J=10.3, 2.0 Hz, 1H), 7.81 (m, 2H), 7.69 (d, J=2.0 Hz, 1H), 7.57 (dd, J=5.0, 0.9 Hz, 1H), 7.29 (d, J=8.5 Hz, 1H), 7.01 (m, 1H), 6.95 (m, 1H), 4.10 (d, J=15.5 Hz, 1H), 4.01 (d, J=15.5 Hz, 1H), 2.65 (m, 2H), 0.78 (t, J=7.0 Hz, 3H); MS (ES) m/z 391 (M−H)−.

Sources & evidence

ORD record: ord-6ea9c135682244c4ae40395cb07df77b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323455B2

Reaction notes

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