3,5-Bis(trifluoromethyl)phenacyl bromide → Methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl](1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylate

HRID 1597103Notes

Reaction equation

HRID 1597103 reaction equation
CC1SC(C([O-])=S)=CC=1.[NH2:10][C:11](=[S:22])[C:12]1[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=1[CH3:17].[F:23][C:24]([F:40])([F:39])[C:25]1[CH:26]=[C:27]([C:35](=O)[CH2:36]Br)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>>[F:23][C:24]([F:39])([F:40])[C:25]1[CH:26]=[C:27]([C:35]2[N:10]=[C:11]([C:12]3[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=3[CH3:17])[S:22][CH:36]=2)[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1

Participants

4

Reactant 3

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromideHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylateHCID 1784259235-Methylthiothiophene-2-carboxylate

Product 1

HCID 86584788Methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl](1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylateYield 5%

Procedure

Methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl]1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylate: A solution of 75 mg (0.3 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge, Cornwall, UK) was reacted with 101 mg (0.3 mmol) of 1-[3,5-bis(trifluoromethyl)phenyl]-2-bromoethane-1-one in a manner similar Example 8, step (a) to give methyl 4-{4-[3,5-bis(trifluoromethyl)phenyl](1,3-thiazol-2-yl)}-5-methylthiothiophene-2-carboxylate (7 mg, 5%) as a solid. 1H-NMR (DMSO-d6; 300 MHz) δ 8.75 (s, 1H), 8.73 (m, 2H), 8.29 (s, 1H), 8.13 (m, 1H), 3.87 (s, 3H), 2.79 (s, 3H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C18H11NO2S3F6, 484.0 (M+H), found 484.0.

Sources & evidence

ORD record
ord-1b22b0ec173c453085e35d6fae915051
Source dataset
uspto-grants-2001_09
Patent number
US06291514B1

Reaction notes

Loading…