Potassium Bromide → HCID 54391518, compound

HRID 231292Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][C:21](C)(C)[CH3:22])=[O:19])=[CH:14][CH:13]=2)=[CH:4][N:3]=1.[K+].[Br-]>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=2)=[CH:4][N:3]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 54425745HCID 54425745, compound

Product 1

HCID 54391518HCID 54391518, compound

Procedure

By substituting an equivalent amount of 3-cyano-2-(4-nitrophenylthio)-5-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyridine in the foregoing procedure there is obtained 2-amino-3-cyano-5-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyridine, which can be alternatively named as 2-amino-3-cyano-5-(4-t-butoxycarbonylstyryl)pyridine; yield 1.14 g (84%) of light yellow crystals, mp 190°-195° C.; NMR (Me2SO-d6) delta 1.57 (s, 9H), 6.57-6.60 (m, 2H), 7.00 (br, 2H), 7.35 (d, 2H, J=8.1 Hz), 7.65 (d, 1H, J=2.7 Hz), 7.84 (d, 2H, J=8.1 Hz), 8.00 (d, 1H, J=2.7 Hz); IR (KBr) 3460, 3360, 2215, 1707, 1623, 1480, 1300, 1287, 1158 cm-1.

Sources & evidence

ORD record: ord-bb1876f1fbbb4d7fbb41ef6c8ade697c
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845216

Reaction notes

Loading…