Sodium Carbonate → HCID 54291610, compound

HRID 1280825Notes

Reaction equation

HRID 1280825 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([CH2:26][CH3:27])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br)([CH3:4])([CH3:3])[CH3:2].[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([CH2:26][CH3:27])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:33]1[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2856454-Fluorophenylboronic acidHCID 53664751HCID 53664751, compound

Product 1

HCID 54291610HCID 54291610, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

[[2-Ethyl-1-(2-bromo-phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester (1.3 g) was combined with 4-fluoro-phenylboronic acid in 20 mL of n-propanol at room temperature. After 30 minutes, the slurry was treated with palladium acetate, triphenylphosphine and 2 mL of 2 M sodium carbonate solution. The mixture was heated at reflux for one hour, cooled to room temperature and diluted with water. After stirring for 1 hour, the mixture was extracted with ethyl acetate, which was washed, dried, filtered, and concentrated to afford 1.1 g of product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. extractionthe mixture was extracted with ethyl acetate, which
  4. washwas washed
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40113fc117b045b59939d5e22359e17b
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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