Trifluoroacetic acid → methyl 3-(4-fluorophenyl)-1H-indole-6-carboxylate

HRID 2365660Notes

Reaction equation

HRID 2365660 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10](C(OC(C)(C)C)=O)[CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596257541-tert-Butyl 6-methyl 3-(4-fluorophenyl)-1H-indole-1,6-dicarboxylate

Product 1

HCID 59625721methyl 3-(4-fluorophenyl)-1H-indole-6-carboxylateYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 53c (705 mg, 1.91 mmol) in CH2Cl2 (4 mL) was added trifluoroacetic acid (1.5 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The resulting mixture was concentrated to give compound 53d (603.3 mg) as a white solid. MS m/z (M+H+) 270.1.

Workup

  1. concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record
ord-ea6f158e689049baae4b7ac94cc82540
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

Loading…