Water → Ethyl 1-(3-isopropylphenyl)-5-trifluoromethyloxy-1H-indole-2-carboxylate

HRID 131643Notes

Reaction equation

HRID 131643 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2.[CH:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([CH3:22])[CH3:21].N1C=CC=CC=1.O>ClCCl.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[CH:20]([C:23]1[CH:28]=[C:27]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:19])=[CH:12][CH:11]=3)[CH:7]=[C:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 2737230ethyl 5-(trifluoromethoxy)-1H-indole-2-carboxylateHCID 27734783-Isopropylbenzeneboronic acid

Product 1

HCID 68698882Ethyl 1-(3-isopropylphenyl)-5-trifluoromethyloxy-1H-indole-2-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.2 g (0.73 mmol) of ethyl 5-trifluoromethyloxy-1H-indole-2-carboxylate, of 0.24 g (1.46 mmol) of 3-isopropylphenylboronic acid, of 0.2 g (1.1 mmol) of copper diacetate and of 0.12 ml (1.46 mmol) of pyridine in 5 ml of dichloromethane is stirred in the presence of 4 Å molecular sieve at ambient temperature for 4 days. The mixture is poured onto 100 ml of water and 50 ml of dichloromethane. The organic phase is separated, washed with 1N hydrochloric acid, dried over magnesium sulfate and then concentrated under reduced pressure. The residue is purified by chromatography on a silica column, elution being carried out with a mixture of cyclohexane and of ethyl acetate. 0.1 g of product is obtained, which product is used as is in the following stage.

Workup

  1. customThe organic phase is separated
  2. washwashed with 1N hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a silica column, elution
  6. additionbeing carried out with a mixture of cyclohexane and of ethyl acetate

Sources & evidence

ORD record
ord-d4dc88ebb7e348b4b5c7e55e63662fb8
Source dataset
uspto-grants-2008_06
Patent number
US07384969B2

Reaction notes

Loading…