Trifluoroacetic acid → Ethyl 2-(indolin-6-yl)thiazole-4-carboxylate

HRID 1896602Notes

Reaction equation

HRID 1896602 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:21]=3)[CH:15]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59418726Ethyl 2-(1-(tert-butoxycarbonyl)indolin-6-yl)thiazole-4-carboxylate

Product 1

HCID 59418774Ethyl 2-(indolin-6-yl)thiazole-4-carboxylateYield 170.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 2-(1-(tert-butoxycarbonyl)indolin-6-yl)thiazole-4-carboxylate (28C) (46 mg, 0.12 mmol) was added DCM (5 ml) and TFA (1 ml) and stirred for 2.5 hours. The mixture was concentrated under reduced pressure to provide 56 mg of the desired product ethyl 2-(indolin-6-yl)thiazole-4-carboxylate (28D): LC/MS (APCI): m/z 275.0 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7f85ab4fb5c42d2976c07d875f6f76e
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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