(3-Cyano-5-fluorophenyl)boronic acid → 3-(5,5-Dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-5-fluorobenzonitrile

HRID 1816898Notes

Reaction equation

HRID 1816898 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]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.[C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[C:22]([F:24])[CH:23]=1)#[N:17]>>[CH3:13][C:7]1([CH3:14])[C:6]2[CH:15]=[C:2]([C:20]3[CH:19]=[C:18]([CH:23]=[C:22]([F:24])[CH:21]=3)[C:16]#[N:17])[CH:3]=[CH:4][C:5]=2[NH:11][C:10](=[O:12])[CH2:9][O:8]1

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 688658147-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 112321363-(5,5-Dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-5-fluorobenzonitrile

Procedure

Prepared from 7-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-cyano-5-fluorophenyl boronic acid generally according to the coupling procedure described in example 1. A white solid: mp 238-239° C.; 1H NMR (DMSO-d6): δ 10.1 (s, 1H), 8.14 (t, J=1.5 Hz, 1H), 7.98 (m, 1H), 7.80 (m, 1H), 7.69 (d, J=1.9 Hz, 1H), 7.64 (dd, J=8.3, 2.0 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 4.27 (s, 2H), 1.63 (s, 6H). MS m/z 309 ([M−H]−); Anal. calcd for C18H15FN2O2: C, 69.67; H, 4.87; N, 9.03. Found: C, 69.51; H, 4.63; N, 9.07

Sources & evidence

ORD record
ord-1c79a1598af64b4788fa6d550def2628
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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