5-Bromo-4-methylthiophene-2-carbonitrile → 4-Methyl-5-(5-methyl-2-oxo-5-thien-2-yl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)thiophene-2-carbonitrile

HRID 1816915Notes

Reaction equation

HRID 1816915 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:18])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:19]=1.Br[C:21]1[S:25][C:24]([C:26]#[N:27])=[CH:23][C:22]=1[CH3:28]>>[CH3:28][C:22]1[CH:23]=[C:24]([C:26]#[N:27])[S:25][C:21]=1[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:18])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:19]=1

Participants

3

Reactant 2

HCID 219862345-Bromo-4-methylthiophene-2-carbonitrileHCID 688661097-Bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 114289474-Methyl-5-(5-methyl-2-oxo-5-thien-2-yl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)thiophene-2-carbonitrile

Procedure

Prepared from 7-bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 5-bromo-4-methylthiophene-2-carbonitrile generally according to the coupling procedure described in examples 82 and 1. 1H-NMR (DMSO-d6) δ 10.26 (s, 1H), 7.83 (s, 1H), 7.56 (dd, J=4.9, 1.1 Hz, 1H), 7.47 (dd, J=8.5, 2.2 Hz, 1H), 7.32 (d, J=2.2 Hz, 1H), 7.29 (d, J=8.5 Hz, 1H), 7.00 (m, 1H), 6.96 (m, 1H), 4.23 (d, J=15.9 Hz, 1H), 4.13 (d, J=15.9 Hz, 1H), 2.19 (s, 3H), 2.03 (s, 3H); MS (ES) m/z 381 (M+H)+; Anal. Calc. For C20H16N2O2S2: C, 63.14, H, 4.24; N, 7.36. Found: C, 62.85, H, 4.16; N, 7.09.

Sources & evidence

ORD record
ord-3a20944371184ddbbfc45db24dcef8bc
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

Loading…