1,2-Dimethoxyethane → 4-Methyl-2-(3,5,3'',5''-tetrafluoro-[1,1';3',1'']terphenyl-5'-yl)-pentanoic acid methyl ester

HRID 426357Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([F:39])[CH:38]=1.C([O-])([O-])=O.[K+].[K+].CO[CH2:51][CH2:52]OC>CCOC(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>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([C:52]2[CH:51]=[C:37]([F:39])[CH:38]=[C:33]([F:32])[CH:34]=2)[CH:12]=[C:13]([C:35]2[CH:34]=[C:33]([F:32])[CH:38]=[C:37]([F:39])[CH:36]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-(3,5-bis-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pentanoic acid methyl ester (104 mg, 0.21 mmol), 3,5-difluorophenylboronic acid (82 mg, 0.52 mmol), K2CO3 solution (2M, 310 μL) and DME (2 mL) was purged with N2 three times before adding Pd(PPh3)4 (10 mg, 0.01 mmol). The mixture was heated at 95° C. overnight (followed by HPLC). The reaction was diluted with EtOAc (5 mL) and then washed successively with NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil. The residue was purified by flash chromatography (0-15% EtOAc in Petroleum ether) to give the title compound (75 mg, 84%) as a yellow oil.

Workup

customwas purged with N2 three times
washwashed successively with NaHCO3 solution and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4aa7ff390f9d42c883af2eb5b8cdd0b3
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106236B2

Reaction notes

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