Potassium Carbonate → HCID 67342557, compound

HRID 1669282Notes

Reaction equation

HRID 1669282 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:37][C:38]([F:49])([F:48])[C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1>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>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:21])([C:22]2[CH:27]=[CH:26][C:25]([C:42]3[CH:43]=[CH:44][C:39]([C:38]([F:49])([F:48])[F:37])=[CH:40][CH:41]=3)=[CH:24][CH:23]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 67341383HCID 67341383, compound

Product 1

HCID 67342557HCID 67342557, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-{4-[1-(4-Bromo-phenyl)-1-hydroxy-heptyl]-benzoylamino}-propionic acid methyl ester (350 mg, 0.74 mmol), potassium carbonate (304 mg, 2.2 mmol), 4-trifluoromethylphenyl boronic acid (279 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium (86 mg, 0.074 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-[1-Hydroxy-1-(4′-trifluoromethyl-biphenyl-4-yl)-heptyl]-benzoylamino}-propionic acid methyl ester (220 mg) as yellow oil.

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-309e079e6efb4c199a2e32d4b21aa314
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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