5-Bromo-2-fluorobenzonitrile → HCID 23435614, compound

HRID 2120741Notes

Reaction equation

HRID 2120741 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH:9]([CH3:11])[O:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.Br[C:16]1[CH:17]=[CH:18][C:19]([F:24])=[C:20]([CH:23]=1)[C:21]#[N:22]>>[F:24][C:19]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[NH:10][CH:9]([CH3:11])[O:8][C:7]([CH3:13])([CH3:12])[C:6]=3[CH:14]=2)=[CH:23][C:20]=1[C:21]#[N:22]

Participants

3

Reactant 2

HCID 27249005-Bromo-2-fluorobenzonitrileHCID 234355746-Bromo-2,4,4-trimethyl-2,4-dihydro-1H-benzo[D][1,3]oxazine

Product 1

HCID 23435614HCID 23435614, compound

Procedure

Prepared according to the coupling procedure for Example 13 from 6-bromo-2,4,4-trimethyl-1,4-dihydro-2H-3,1-benzoxazine and 5-bromo-2-fluorobenzonitrile. A white solid: mp 184-186° C.; 1H-NMR (DMSO-d6) δ 8.17 (dd, 1H, J=5.86, 3.42 Hz), 8.00-7.98 (m, 1H), 7.52 (t, 1H, J=9.28 Hz), 7.45 (d, 1H, J=1.95 Hz), 7.34 (dd, 1H, J=8.30, 1.95 Hz), 6.63 (d, 1H, J=8.3 Hz), 6.45 (d, 1H), 4.8 (q, 1H, J=5.37 Hz), 1.53 (s, 3H), 1.49 (s, 3H), 1.29 (d, 3H, J=5.37 Hz); MS (ES) m/z 297 ([M+H]+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-aaa84e8b3ea14d4f98099840393d9ac1
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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