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

HRID 644108Notes

Reaction equation

HRID 644108 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].Br.C(O)(=O)C>C(O)(=O)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

5

Reactant 3

HCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indoleHCID 5323651Methyl 3-methoxyacrylateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 11221407methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylateYield 8.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.27 g of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, 1.16 g of methyl trans-3-methoxyacrylate and 12 mL of glacial acetic acid were mixed, then, 797 mg of 30 wt % hydrogen bromide/acetic acid solution was added dropwise into the mixture at an inner temperature of 25° C., the mixture was stirred for 5 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 0.15 g of methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate (yellow solid). Yield: 8%.

Workup

  1. customa reaction
  2. customAfter completion of the reaction

Sources & evidence

ORD record
ord-9b60ea2565b24b14a14ac677ad3b821f
Source dataset
uspto-grants-2010_04
Patent number
US07700642B2

Reaction notes

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