Triethylamine → 4-(2-Chloro-2-fluoro-acetylamino)-thiophene-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][S:7][CH:6]=1)=[O:4].[Cl:11][CH:12]([F:16])[C:13](Cl)=[O:14].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:13](=[O:14])[CH:12]([Cl:11])[F:16])=[CH:8][S:7][CH:6]=1)=[O:4]Participants
5
Conditions
- Temperature
- -15 °C
Procedure
To a suspension of 4-amino-thiophene-3-carboxylic acid methyl ester (2 g) in dichloromethane (25 mL) was added chlorofluoroacetyl chloride (1.16 mL) and the reaction mixture was stirred to −15° C. Then a solution of triethylamine (3.2 mL) in dichloromethane (5 mL) was added slowly to the cold reaction mixture which was then allowed to warm up and stirred at room temperature for one hour. The reaction mixture was then diluted with further methylene chloride and washed several times with water, dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a light yellow solid. MS (EI): 251.1; mp=51-54° C.
Workup
- temperatureto warm up
- stirringstirred at room temperature for one hour
- washwashed several times with water
- dry with materialdried with sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-c6e3df7467934230baa553f943caa245
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732452B2
Reaction notes
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