3-Bromo-5-fluorobenzonitrile → 3-Fluoro-5-(2,2,4,4-tetramethyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-benzonitrile

HRID 277871Notes

Reaction equation

HRID 277871 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9]([CH3:12])([CH3:11])[O:8][C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.Br[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([F:25])[CH:24]=1)[C:20]#[N:21]>>[F:25][C:23]1[CH:22]=[C:19]([CH:18]=[C:17]([C:2]2[CH:3]=[CH:4][C:5]3[NH:10][C:9]([CH3:12])([CH3:11])[O:8][C:7]([CH3:14])([CH3:13])[C:6]=3[CH:15]=2)[CH:24]=1)[C:20]#[N:21]

Participants

3

Reactant 2

HCID 27833303-Bromo-5-fluorobenzonitrileHCID 23435577HCID 23435577, compound

Product 1

HCID 183745613-Fluoro-5-(2,2,4,4-tetramethyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-benzonitrile

Procedure

Prepared using the coupling procedure for Example 13 starting with 6-bromo-2,2,4,4-tetramethyl-1,4-dihydro-2H-3,1-benzoxazine and 3-bromo-5-fluorobenzonitrile. A white solid: 1H-NMR (DMSO-d6) δ 8.03 (s, 1H), 7.87 (d, 1H, J=10.7 Hz), 7.65 (d, 1H, J=10.7 Hz), 7.57 (d, 1H, J=1.98 Hz) 7.45 (dd, 1H, J=8.33, 1.98 Hz), 6.65 (d, 1H, J=8.33 Hz), 6.42 (s, 1H), 1.52 (s, 6H), 1.34 (s, 6H); MS (ES) m/z 311 ([M+H]+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-069f3985f6da487fb7f399b4061769ea
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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