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

HRID 644099Notes

Reaction equation

HRID 644099 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.[CH3:20][O:21][CH:22]([O:28]C)[CH2:23][C:24](OC)=O.C(O)(=O)C.P(Cl)(Cl)(Cl)=O>O>[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:24]=[CH:23]/[C:22]([O:21][CH3:20])=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24813Phosphorus oxychlorideHCID 81924Methyl 3,3-dimethoxypropionateHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole

Product 1

HCID 11221407methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.01 g of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, 0.92 g of methyl 3,3-dimethoxypropionate, 0.72 mL of 90 wt % aqueous acetic acid (containing 4 mmol of water) and 6 mL of glacial acetic acid were mixed, then, 0.33 g of phosphorus oxychloride was added dropwise into the mixture at an inner temperature of 25° C., the added mixture was stirred for 9 hours at the same temperature to cause a reaction. After completion of the reaction, 16 mL of water was added dropwise into the reaction liquid, and the precipitated crystals were filtrated. The crystals were washed with 20 vol % aqueous methanol, then, dried to obtain 1.25 g of methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate (yellow solid). Yield: 93%.

Workup

  1. customa reaction
  2. additionwas added dropwise into the reaction liquid
  3. filtrationthe precipitated crystals were filtrated
  4. washThe crystals were washed with 20 vol % aqueous methanol
  5. customdried

Sources & evidence

ORD record
ord-48131c1023294c24b2c8e89200d34f81
Source dataset
uspto-grants-2010_04
Patent number
US07700642B2

Reaction notes

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