1,2-Dibromoethane → Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

HRID 1476513Notes

Reaction equation

HRID 1476513 reaction equation
NC1C=CSC=1C(OC)=O.[F:11][C:12]([F:26])([F:25])[C:13]([NH:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]([O:23][CH3:24])=[O:22])=[O:14].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([Li])CCC.[Br:45]CCBr>>[Br:45][C:19]1[S:18][C:17]([C:21]([O:23][CH3:24])=[O:22])=[C:16]([NH:15][C:13](=[O:14])[C:12]([F:11])([F:25])[F:26])[CH:20]=1

Participants

6

Reactant 5

HCID 78391,2-DibromoethaneHCID 9845Trifluoroacetic anhydrideHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 2805185Methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 56965789Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Procedure

In reaction scheme 5 the synthesis of compound B53 is described. The intermediate 3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester (compound B54b) is obtained according to a procedure described in literature (Bioorganic & Medicinal Chemistry Letters 17 (2007) 2535-2539) by conversion of methyl 3-aminothiophene-2-carboxylate to methyl 3-[(trifluoroacetyl)amino]thiophene-2-carboxylate with trifluoroacetic acid anhydride followed by a lithiation/bromination sequence using n-butyllithium and 1,2-dibromoethane to give methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate which is hydrolysed under basic conditions using potassium carbonate to obtain 3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester (compound B54b).

Sources & evidence

ORD record
ord-1675147131ea48a098e32004fae6180c
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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