3-Methylbenzyl alcohol → Ethyl 5-trifluoromethyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxylate

HRID 1911245Notes

Reaction equation

HRID 1911245 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[CH3:19][C:20]1[CH:21]=[C:22]([CH2:26]O)[CH:23]=[CH:24][CH:25]=1.C(C=P(CCCC)(CCCC)CCCC)#N>>[F:18][C:2]([F:17])([F:1])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2

Participants

4

Reactant 3

HCID 114763-Methylbenzyl alcoholHCID 4622928CyanomethylenetributylphosphoraneHCID 17389890Ethyl 5-(trifluoromethyl)-1H-indole-2-carboxylate

Product 1

HCID 66890014Ethyl 5-trifluoromethyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxylateYield 80.3%

Conditions

Temperature
110 °C

Procedure

This compound was prepared by reacting 333 mg (1.295 mmol) of ethyl 5-trifluoromethyl-1H-indole-2-carboxylate with 0.31 mL (2.59 mmol) of 3-methylphenylmethanol in the presence of 0.92 g (3.826 mmol) of (cyanomethylene)tributylphosphorane (CMBP). The reaction mixture is stirred at 110° C. for 15 hours and then concentrated to dryness. The crude reaction product is then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate, to give 376 mg of the expected product in the form of an oil.

Workup

  1. customThis compound was prepared
  2. concentrationconcentrated to dryness
  3. customThe crude reaction product
  4. customis then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-5d064c1770614389879753d10410d815
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

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