Formic Acid → 2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

HRID 2249695Notes

Reaction equation

HRID 2249695 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O)=O.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:21]([O:20][C:18]([C:3]1[N:4]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10]([CH:2]=1)=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=2)=[O:19])[CH3:22]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 178165173-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

Product 1

HCID 178165142-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acidYield 50.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 6 ml of N,N-dimethylformamide are suspended 0.30 g of 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid, 0.10 g of tetrakis(triphenylphosphine)palladium(0), 0.24 ml of formic acid and 1.36 ml of triethylamine. The suspension is stirred at 80° C. for 5 hours. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 0.12 g of 2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid as a yellow solid product.

Workup

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-1382030b41e14a70810f10919f346476
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…