N-(4-bromo-2-fluorophenyl)acetamide → N-[4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-2-fluorophenyl]-acetamide

HRID 413191

Reaction equation

HRID 413191 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[C:4]([F:12])[CH:3]=1.[CH3:13][C:14]1([CH3:28])[C:19]2[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:18]=2[NH:17][C:16](=[O:27])[O:15]1>>[CH3:13][C:14]1([CH3:28])[C:19]2[CH:20]=[C:21]([C:2]3[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[C:4]([F:12])[CH:3]=3)[CH:22]=[CH:23][C:18]=2[NH:17][C:16](=[O:27])[O:15]1

Participants

3

Reactant 2

HCID 67593N-(4-bromo-2-fluorophenyl)acetamideHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 23509628N-[4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-2-fluorophenyl]-acetamide

Procedure

Prepared according to procedure B from 4′-bromo-2′-fluoroacetanilide and (1,4-dihydro4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid. Off white solid ; mp 245-247° C. 1H-NMR (DMSO-d6) δ10.3 (s,1H), 9.79 (s, 1H), 7.95 (t,1H; J=8.4 Hz), 7.56-7.63(m,3H), 7.47(dd,1H J=1.64, 8.47 Hz), 6.95(d,1H; J=8.9 Hz), 2.1(s, 3H), 1.67(s,6H); MS+APCI [M+H]+ m/z 329. Anal. Calc. For C18H17N2 FO3: C, 65.85, H, 5.22, N, 8.53. Found: C,65.46, H,5.24, N,8.12.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bda679887b3e4c2181b5fd8c0f3d5635
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Linked notes

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