Potassium Carbonate → HCID 67153483, compound

HRID 1160882Notes

Reaction equation

HRID 1160882 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][NH:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:19][C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]([F:48])([F:47])[O:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1>>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][NH:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:19][C:20]2[CH:25]=[CH:24][C:23]([C:41]3[CH:40]=[CH:39][C:38]([O:37][C:36]([F:35])([F:47])[F:48])=[CH:43][CH:42]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 67153603HCID 67153603, compound

Product 1

HCID 67153483HCID 67153483, compoundYield 71.8%

Procedure

3-{4-[1-(4-bromo-phenylsulfanyl)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (350 mg, 0.75 mmol), potassium carbonate (311 mg, 2.25 mmol), 4-trifluoromethoxylphenyl boronic acid (311 mg, 1.5 mmol) and tetrakis-(triphenylphosphine)palladium (87 mg, 0.075 mmol) are place in a flask. After the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml) is added. The resulting solution is refluxed overnight, loaded on silica gel, eluted with hexane and ethyl acetate to give 3-{4-[3-Methyl-1-(4′-trifluoromethoxy-biphenyl-4-ylsulfanyl)-butyl]-benzoylamino}-propionic acid methyl ester (294 mg) as a yellow solid.

Workup

  1. customAfter the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml)
  2. additionis added
  3. temperatureThe resulting solution is refluxed overnight
  4. washeluted with hexane and ethyl acetate

Sources & evidence

ORD record
ord-3e2177d76cdc493dbcf677a563a15f5d
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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