4-Bromothiophene-2-carbonitrile → 4-[2-(Trifluoromethyl)-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazine-6-yl]-2-thiophenecarbonitrile

HRID 277869Notes

Reaction equation

HRID 277869 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.Br[C:19]1[CH:20]=[C:21]([C:24]#[N:25])[S:22][CH:23]=1>>[CH3:15][C:7]1([CH3:16])[C:6]2[CH:17]=[C:2]([C:19]3[CH:20]=[C:21]([C:24]#[N:25])[S:22][CH:23]=3)[CH:3]=[CH:4][C:5]=2[NH:10][CH:9]([C:11]([F:14])([F:13])[F:12])[O:8]1

Participants

3

Reactant 2

HCID 142923554-Bromothiophene-2-carbonitrileHCID 234355726-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine

Product 1

HCID 234355804-[2-(Trifluoromethyl)-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazine-6-yl]-2-thiophenecarbonitrile

Procedure

Prepared using the coupling procedure for Example 13 starting with 6-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine and 4-bromo-2-thiophenecarbonitrile. A yellow solid: 1H-NMR (DMSO-d6) δ 8.43 (s, 1H), 8.19 (s, 1H), 7.54 (d, 1H, J=1.98 Hz), 7.46 (dd, 1H, J=8.33, 1.98 Hz), 6.90 (s, 1H), 6.83 (d, 1H, J=8.33 Hz), 5.35 (d, 1H, J=3.57 Hz), 1.59 (s, 3H), 1.57 (s, 3H); MS (ES) m/z 337 ([M−H]−).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-25488e7c31f649b295345d53079b428c
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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