4-Bromothiophene-2-carbonitrile → 4-(4,4-Dicyclopropyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile

HRID 1634960Notes

Reaction equation

HRID 1634960 reaction equation
[CH:1]1([C:4]2([CH:18]3[CH2:20][CH2:19]3)[C:9]3[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][C:8]=3[NH:7][C:6](=[O:17])[O:5]2)[CH2:3][CH2:2]1.Br[C:22]1[CH:23]=[C:24]([C:27]#[N:28])[S:25][CH:26]=1>>[CH:1]1([C:4]2([CH:18]3[CH2:20][CH2:19]3)[O:5][C:6](=[O:17])[NH:7][C:8]3[CH:13]=[CH:12][C:11]([C:22]4[CH:23]=[C:24]([C:27]#[N:28])[S:25][CH:26]=4)=[CH:10][C:9]2=3)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 142923554-Bromothiophene-2-carbonitrileHCID 23509592(4,4-dicyclopropyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 98808904-(4,4-Dicyclopropyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile

Procedure

The title compound was prepared according to Procedure B from (4,4-dicyclopropyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 4-bromo-2-thiophene carbonitrile. A white solid: mp 244-245° C.; 1H-NMR (DMSO-d6) δ10.25 (s, 1H), 8.49 (d, 1H, J=0.87 Hz), 8.33 (s, 1H), 7.74 (d, 1H, J=1.44 Hz), 7.67 (dd, 1H, J=8.28, 1.54 Hz), 6.90 (d, 1H, J=8.28 Hz), 1.53 (m, 2H), 0.59-0.41 (m, 6H), 0.31-0.24 (m, 2H); MS (ESI) m/z 335 ([M−H]−, 100%); Anal. Calc. For C19H16N2O2S: C, 67.84, H, 4.79, N, 8.33. Found: C, 64.92, H, 4.66, N, 7.71.

Sources & evidence

ORD record
ord-ff9289a120d340fd93d2791a7ddb410c
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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