Water → methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate

HRID 644106Notes

Reaction equation

HRID 644106 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([CH3:19])[CH3:18])[CH:9]=2)=[CH:4][CH:3]=1.CO/[CH:22]=[CH:23]/[C:24]([O:26][CH3:27])=[O:25].O.P(Cl)(Cl)(Cl)=O>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([CH3:19])[CH3:18])[C:9]=2/[CH:22]=[CH:23]/[C:24]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indoleHCID 5323651Methyl 3-methoxyacrylate

Product 1

HCID 11221407methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylateYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.31 g of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, 0.28 g of methyl trans-3-methoxyacrylate, 36 mg of water and 6 mL of acetonitrile were mixed, then, 164 mg of phosphorus oxychloride was added dropwise into the mixture at an inner temperature of 25° C., the added mixture was stirred for 22 hours at the same temperature to cause a reaction. After completion of the reaction, the same post treatment was conducted as in Example 1 to obtain 0.21 g of methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate (yellow solid). Yield: 51%.

Workup

  1. customa reaction
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-6351684ae73844d5a6a2ffbed1ac7132
Source dataset
uspto-grants-2010_04
Patent number
US07700642B2

Reaction notes

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