Ethyl trifluoroacetate → N-(3-(4-bromothiophen-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

HRID 63304

Reaction equation

HRID 63304 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:6]1[S:7][CH:8]=[C:9]([Br:11])[CH:10]=1)[OH:5].[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15]>C(Cl)Cl>[Br:11][C:9]1[CH:10]=[C:6]([CH:4]([OH:5])[CH2:3][CH2:2][NH:1][C:14](=[O:15])[C:13]([F:20])([F:19])[F:12])[S:7][CH:8]=1

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 82291520HCID 82291520, compound

Product 1

HCID 86694591N-(3-(4-bromothiophen-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-1-(4-bromothiophen-2-yl)propan-1-ol and ethyl trifluoroacetate (2.0 mL) were stirred in CH2Cl2 (10 mL) at room temperature overnight. Concentration under reduced pressure gave N-(3-(4-bromothiophen-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide which was used in the next step without additional purification. Yield (0.77 g, 28% in three steps); 1H NMR (400 MHz, DMSO-d6) δ 9.36 (br.s, 1H), 7.51 (d, J=1.5 Hz, 1H), 6.90-7.00 (m, 1H), 5.86 (d, J=5.0 Hz, 1H), 4.75-4.83 (m, 1H), 3.20-3.30 (m, 2H), 1.80-1.94 (m, 2H).

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-08ef64ba31ce4fd3a324136e04e0ae93
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Linked notes

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