5-Bromo-4-methylthiophene-2-carbonitrile → 5(2-Methylspiro[4H-3,1-benzoxazine-4,1'-cyclopentane]-6-yl)-4 methyl-2-thiophenecarbonitrile

HRID 2120734

Reaction equation

HRID 2120734 reaction equation
[CH3:1][C:2]1[O:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:4]=2[N:3]=1.Br[C:18]1[S:22][C:21]([C:23]#[N:24])=[CH:20][C:19]=1[CH3:25]>>[CH3:1][C:2]1[O:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:6]=[C:7]([C:18]3[S:22][C:21]([C:23]#[N:24])=[CH:20][C:19]=3[CH3:25])[CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 219862345-Bromo-4-methylthiophene-2-carbonitrileHCID 234355852-methyl-6-bromospiro[4H-3,1-benzoxazine-4,1'-cyclopentane]

Product 1

HCID 234355965(2-Methylspiro[4H-3,1-benzoxazine-4,1'-cyclopentane]-6-yl)-4 methyl-2-thiophenecarbonitrile

Procedure

The title compound was prepared according to the procedure for Example 13 from 2-methyl-6-bromospiro[4H-3,1-benzoxazine-4,1′-cyclopentane] and 5-bromo-4-methyl-2-thiophenecarbonitrile. A yellowish solid: mp 58-60° C.; 1H-NMR (DMSO-d6) δ 7.79 (s, 1H), 7.16 (d, 1H, J=1.9 Hz), 7.12 (dd, 1H, J=8.4, 2.2 Hz), 6.66 (s, 1H), 6.63 (d, 1H, J=8.4 Hz), 4.75 (m, 1H), 2.26 (s, 3H), 2.14 (m, 1H), 1.87 (m, 1H), 1.4-1.7 (m, 6H), 1.32 (d, 3H, J=5.5 Hz).

Sources & evidence

ORD record
ord-70ca097b4a3d4dc3a3983847e8dea3bb
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Linked notes

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