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

HRID 2298614Notes

Reaction equation

HRID 2298614 reaction equation
[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=1[CH3:8].[F:14][C:15]([F:31])([F:30])[C:16]1[CH:17]=[C:18]([C:26](=O)[CH2:27]Br)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1>>[F:14][C:15]([F:30])([F:31])[C:16]1[CH:17]=[C:18]([C:26]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=3[CH3:8])[S:13][CH:27]=2)[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

3

Reactant 2

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromideHCID 86583815Methyl 4-(aminothioxomethyl)-5-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

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) δ8.75 (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-a14a99e8674c4b8daabf8974c0a61ae8
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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