Trifluoroacetic acid → 2-Amino-5-chloro-3-phenylthiophene

HRID 1639525Notes

Reaction equation

HRID 1639525 reaction equation
C([NH:8][C:9]1[S:10][C:11]([Cl:20])=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl.CN(C=O)C>[NH2:8][C:9]1[S:10][C:11]([Cl:20])=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589117542-(N-Boc-amino)-5-chloro-3-phenyl-thiophene

Product 1

HCID 589118102-Amino-5-chloro-3-phenylthiophene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(N-Boc-amino)-5-chloro-3-phenyl-thiophene (66 mg, 0.21 mmol) was treated with trifluoroacetic acid (1 ml) in dichloromethane (3 ml) at ambient temperature for 1 hr. The mixture was diluted with DMF (1 ml) and the more volatile materials removed under reduced pressure. The resulting DMF solution of 2-amino-5-chloro-3-phenylthiophene was used in the subsequent coupling step without purification.

Workup

  1. customthe more volatile materials removed under reduced pressure
  2. customThe resulting DMF solution of 2-amino-5-chloro-3-phenylthiophene was used in the subsequent coupling step without purification

Sources & evidence

ORD record
ord-0c37156463a54146978ac7ba121f5620
Source dataset
uspto-grants-2012_02
Patent number
US08110568B2

Reaction notes

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