1,3-Dichloroacetone → 3-(4-chloromethyl-oxazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

HRID 644059Notes

Reaction equation

HRID 644059 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]([NH2:21])=[O:20])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:22][CH2:23][C:24]([CH2:26]Cl)=O>C1(C)C=CC=CC=1.ClCCl>[Cl:22][CH2:23][C:24]1[N:21]=[C:19]([C:10]2[C:11]3[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:9]=2)[O:20][CH:26]=1

Participants

5

Reactant 2

HCID 107931,3-DichloroacetoneHCID 686974651-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid amide

Product 1

HCID 686996223-(4-chloromethyl-oxazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indoleYield 81.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid amide (500 mg, 1.75 mmol) in toluene (4 ml) was added 1,3-dichloroacetone (333 mg, 2.62 mmol) and the reaction mixture subjected to microwave irradiation at 150° C. for 30 minutes. The resulting black solution was diluted with dichloromethane (50 ml) and washed with 5% aqueous sodium carbonate solution (5×20 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The resulting brown oil was purified by flash column chromatography using 5% (v/v) acetone in petroleum ether 40-60 to give 3-(4-chloromethyl-oxazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (510 mg, 1.42 mmol) as a white solid.

Workup

  1. customirradiation at 150° C. for 30 minutes
  2. washwashed with 5% aqueous sodium carbonate solution (5×20 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe resulting brown oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-9716f507e23745e1a5bd37dd8b5e53e3
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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