2-Ethynylthiophene → (E)-3-(4-oxo-7-(2-(thiophen-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrile

HRID 859515Notes

Reaction equation

I[C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[C:22]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)#[CH:23]>>[O:11]=[C:9]1[CH2:8][C:7]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])=[N:6][C:5]2[CH:20]=[CH:21][C:2]([C:23]#[C:22][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[CH:3][C:4]=2[NH:10]1

Participants

Reactant 2

HCID 52462582-Ethynylthiophene

HCID 222246583-(7-Iodo-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

Product 1

HCID 22224682(E)-3-(4-oxo-7-(2-(thiophen-2-yl)ethynyl)-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)benzonitrileYield 82.8%

Procedure

Prepared from 3-(7-iodo-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile (Example 50) (185 mg, 0.48 mmol) and 2-ethynylthiophene (78 mg, 0.72 mmol) [prepared from 2-thiophenecarboxaldehyde according to J. Org. Chem. 1982, 47, 2201–2204] according to the general procedure F. Obtained as a light yellow solid (146 mg).

Sources & evidence

ORD record: ord-f4f87e8011e24be59890c65bd297e788
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151098B2

Reaction notes

Loading…