2-(4-Bromo-2-fluorophenyl)acetonitrile → HCID 23509618, compound

HRID 413189Notes

Reaction equation

HRID 413189 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1([CH3:27])[C:18]2[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:17]=2[NH:16][C:15](=[O:26])[O:14]1>>[CH3:12][C:13]1([CH3:27])[O:14][C:15](=[O:26])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([F:11])[CH:3]=3)=[CH:19][C:18]1=2

Participants

3

Reactant 2

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 23509618HCID 23509618, compound

Procedure

Prepared according to procedure B from 4-bromo-2-fluorophenylacetonitrile (T. Alessi A. H. P. U.S. Pat. No: 4,895,862) and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid. A grey solid; mp 253-256° C. 1HNMR(DMSO-d6) □10.35 (s,1H) 7.67-7.49(m,5H), 6.97(d,1H; J=8.6 Hz) 4.09 (s,2H) (s,2H) 1.67(s,6H); MS [M−H]− m/z 309. Anal. Calc. For C18H15N2FO2.0.15H20: C,69.07, H, 4.93, N, 8.95. Found C,69.27, H 5.05, N, 8.50

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-364f003385214c90bfa739fa6e73151e
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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