3-Bromothiophene → HCID 13586593, compound

HRID 1242979Notes

Reaction equation

HRID 1242979 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][NH:8][CH:9]=[O:10]>[Cu]I>[CH3:7][N:8]([C:2]1[CH:6]=[CH:5][S:4][CH:3]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 133833-BromothiopheneHCID 31254N-Methylformamide

Product 1

HCID 13586593HCID 13586593, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

Using general procedure C with the exception that CuI (10 mg, 0.05 mmol, 5 mol %) was used, 3-bromothiophene was coupled with N-methylformamide with the reaction time of 24 h. Chromatography gave 114 mg (81%) of the title compound as an oil. 1H NMR (CDCl3, 300 MHz): δ 8.36 (s, 0.8H), 7.71 (s, 0.2H), 7.49 (dd, 0.2H, J=1.5, 5.4 Hz), 7.08 (dd, 0.2H, J=1.2, 3.0 Hz), 6.80 (dd, 0.2H, J=3.3, 5.4 Hz), 6.64 (dd, 0.8H, J=3.3, 5.1 Hz), 6.30 (dd, 0.8H, J=1.8, 5.4 Hz), 5.98 (dd, 0.8H, J=1.2, 3.0 Hz), 2.79 (s, 2.4H), 2.21 (s, 0.6H).

Sources & evidence

ORD record
ord-9aa8f5db267548c19ef177733ffb54c2
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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