(3-Chlorophenyl)boronic acid → 2-(Trifluoromethyl)-4,4-dimethyl-6-(3-chlorophenyl)-1,4-dihydro-2H-3,1-benzoxazine

HRID 2120749Notes

Reaction equation

HRID 2120749 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH:9]([C:11]([F:14])([F:13])[F:12])[O:8][C:7]([CH3:16])([CH3:15])[C:6]=2[CH:17]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[CH:4][C:5]3[NH:10][CH:9]([C:11]([F:14])([F:13])[F:12])[O:8][C:7]([CH3:16])([CH3:15])[C:6]=3[CH:17]=2)[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 234355726-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine

Product 1

HCID 234356022-(Trifluoromethyl)-4,4-dimethyl-6-(3-chlorophenyl)-1,4-dihydro-2H-3,1-benzoxazine

Procedure

Prepared according to the coupling procedure for Example 17 from 6-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine and 3-chlorophenyl boronic acid. A yellowish solid: mp 108-109° C.; 1H-NMR (DMSO-d6) δ 7.69 (t, 1H, J=1.7 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.35-7.50 (m, 3H), 7.32 (dt, 1H, J=8.1, 1.1 Hz), 6.91 (s, 1H), 6.87 (d, 1H, J=8.4 Hz), 5.35 (m, 1H), 1.60 (s, 3H), 1.59 (s, 3H); MS (ESI) m/z 340 [M−H]−.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-21dcf7f5ac354a46b230772b40a1121e
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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