Water → 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid

HRID 514249Notes

Reaction equation

HRID 514249 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:13](=[O:30])[NH:14][CH:15]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:16]([F:19])([F:18])[F:17])[N:8]2[CH2:11][CH3:12])=[CH:4][C:3]=1[C:31]([O:33]CC)=[O:32].B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:13](=[O:30])[NH:14][CH:15]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:16]([F:17])([F:18])[F:19])[N:8]2[CH2:11][CH3:12])=[CH:4][C:3]=1[C:31]([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86713972ethyl 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate

Product 1

HCID 867139736-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Ethyl 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (0.10 g, 0.19 mmol) was dissolved in 5 ml of dichloromethane and a solution of boron tribromide in dichloromethane (0.96 ml, 0.96 mmol) was added dropwise at −10° C. The reaction mixture was stirred at −10° C. for 1 h and then at room temperature for 2 h. Water was added and the precipitated solid was filtered off with suction and dried. 0.077 g (71% of theory) of 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid was obtained.

Workup

  1. waitat room temperature for 2 h
  2. filtrationthe precipitated solid was filtered off with suction
  3. customdried

Sources & evidence

ORD record
ord-073aa265d69e47a1be4a58b39a5c2351
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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