Triethylamine → 2-[5-(3-Isopropyl-phenoxy)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester

HRID 226513Notes

Reaction equation

HRID 226513 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH:12]=[C:13]([OH:15])[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[CH:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)([CH3:29])[CH3:28].C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=2)[CH:12]=[C:13]([O:15][C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([CH:27]([CH3:29])[CH3:28])[CH:35]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27734783-Isopropylbenzeneboronic acidHCID 577549412-(5-Hydroxy-4'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester

Product 1

HCID 577550542-[5-(3-Isopropyl-phenoxy)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (50 mg, 0.14 mmol), 3-isopropylphenyl boronic acid (45 mg, 0.27 mmol), copper acetate (26 mg, 0.14 mmol), triethylamine (57 μL, 0.4 mmol) and powdered 4 Å molecular sieves in DCM (1 mL) were stirred at room temperature for 2 days. The reaction mixture was concentrated in vacuo. Purification by flash chromatography (EtOAc:petroleum ether) give the title compound (32 mg, 48%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification by flash chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-6a061b6a9608462492b50c820c07fdc1
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

Loading…