Trifluoroacetic acid → HCID 86713872, compound

HRID 521934Notes

Reaction equation

HRID 521934 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2(O)[CH2:12][CH2:11][O:10][CH2:9]2)[CH:5]=[C:4]([F:14])[C:3]=1[C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=1.FC1C=C(C2(O)CCOC2)C=C(F)C=1C1SC=C(C(O)=O)N=1.FC(F)(F)C(O)=O>ClCCl>[O:10]1[CH2:11][CH:12]=[C:8]([C:6]2[CH:7]=[C:2]([F:1])[C:3]([C:15]3[S:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=3)=[C:4]([F:14])[CH:5]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86713871HCID 86713871, compoundHCID 86713873HCID 86713873, compound

Product 1

HCID 86713872HCID 86713872, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 2-[2,6-difluoro-4-(3-hydroxytetrahydrofuran-3-yl)phenyl]thiazole-4-carboxylate (250 mg, 0.732 mmol, precursor to Intermediate 144) in dichloromethane (1 mL) was added TRIFLUOROACETIC ACID (1 mL) The mixture was heated at 120° C. in microwave for 2 h. After in vacuo concentration, purification by CombiFlash (0 to 100% EtOAC in heptane) provided methyl 2-(4-(2,5-dihydrofuran-3-yl)-2,6-difluorophenyl)thiazole-4-carboxylate (57 mg, 24% yield) as a mixture of olefin isomers.

Workup

  1. concentrationAfter in vacuo concentration, purification by CombiFlash (0 to 100% EtOAC in heptane)

Sources & evidence

ORD record
ord-37dd4e403dfe47f6ac70079ef6d3a650
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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