(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid → 3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)-5-fluoro-phenylacetonitrile

HRID 1725078Notes

Reaction equation

HRID 1725078 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[C:6]([F:8])[CH:7]=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:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[C:6]([F:8])[CH:7]=3)=[CH:19][C:18]1=2

Participants

3

Reactant 2

HCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acidHCID 235096352-(3-Bromo-5-fluorophenyl)acetonitrile

Product 1

HCID 227366313-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]-oxazin-6-yl)-5-fluoro-phenylacetonitrile

Procedure

The title compound was prepared according to the procedure B from 3-bromo-5-fluorophenylacetonitrile and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1 -benzoxazin-6-yl)boronic acid. A white solid was obtained and recrystallized from ethanol/ether: mp 218-220. 1H NMR (DMSO-d6) δ 1.67 (s, 6H), 4.11 (s, 2H), 6.98 (d, 1H, J=8.92 Hz), 7.18 (d, 1H, J=9.26 Hz), 7.52-7.62 (m, 3H), 10.37 (s, 1H); MS(EI) (M−H)31 m/z 309; Anal. Calcd. For C18H15FN2O2: C, 69.67; H, 4.87; N, 9.03. Found: C, 69.78; H, 4.97; N, 8.36.

Workup

  1. customA white solid was obtained
  2. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-2b79887451ad4d09babe45f9386af606
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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