Sodium Carbonate → HCID 57665919, compound

HRID 889693Notes

Reaction equation

HRID 889693 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[F:35][C:36]([F:53])([F:52])[C:37]1[N:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=[CH:39][CH:38]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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>[CH2:1]([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=2)[CH:13]=[C:14]([C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([C:36]([F:35])([F:52])[F:53])[N:42]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 177504992-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridineHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57665919HCID 57665919, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To 4-Methyl-2-(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester, compound 1g (1.09 mg, 2.13 mmol) in dimethoxyethane (15 ml), was added 6-(Trifluoromethyl)pyridine-2-boronic acid pinacol ester (750 mg, 2.56 mmol), and 2M Na2CO3 (2.1 mL, 4.26 mmol). The mixture was degassed, tetrakis(triphenylphosphine)palladium (0) (490 mg, 0.426 mmol) was added and the mixture was degassed, and then heated to 80° C. After 1 hr, the reaction was cooled to room temperature, diluted with EtOAc and washed with NaHCO3 and brine. Purification by column chromatography gave the title compound (987 mg, 91%). Calcd for C27H25F6NO2 (M+H) 509.44, Found 510.3.

Workup

  1. customThe mixture was degassed
  2. customthe mixture was degassed
  3. temperaturethe reaction was cooled to room temperature
  4. additiondiluted with EtOAc
  5. washwashed with NaHCO3 and brine
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-14dde9d73ed34289a2372c24e6e05575
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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