4-Bromo-2-fluoroanisole → 6-(3-Fluoro-4-methoxy-phenyl)4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1635002Notes

Reaction equation

HRID 1635002 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][C:12]1([CH3:26])[C:17]2[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:16]=2[NH:15][C:14](=[O:25])[O:13]1>>[F:10][C:4]1[CH:3]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]3[NH:15][C:14](=[O:25])[O:13][C:12]([CH3:26])([CH3:11])[C:17]=3[CH:18]=2)[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 753784-Bromo-2-fluoroanisoleHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 235096406-(3-Fluoro-4-methoxy-phenyl)4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared according to procedure B from 4-bromo-2-fluoroanisole and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid. White solid: mp 210-211° C. 1H-NMR (DMSO-d6), δ10.27(s,1H), 7.52-7.60 (m,3H), 7.45 (d,1H, J=8.6 Hz), 7.22 (t, 1H; J=8.9 Hz), 6.94 (d,1H, J=8.8 Hz), 3.87 (s,3H), 1.66 (s, 6H). MS [M−H]−m/z=300. Anal. Calc. For C17H16FNO3: C, 67.76, H, 5.35, N, 4.65. Found: C,67.88, H,5.39, N, 4.70.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7b1054c3fe7547feab86b4b93fc8d195
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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