Water → HCID 117760118, compound

HRID 1049517Notes

Reaction equation

HRID 1049517 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22](OS(C(F)(F)F)(=O)=O)=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.F[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=C[C:40]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O.C[N:58](C=O)C>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>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C:22]([C:44]4[CH:39]=[CH:40][N:58]=[C:42]([O:45][CH3:46])[CH:43]=4)=[N:21][CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 117760141HCID 117760141, compound

Product 1

HCID 117760118HCID 117760118, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

Under an argon atmosphere, to a solution of ethyl 3-cyclopropyl-3-(3-(((5-neopentyl-6-(((trifluoromethyl)sulfonyl)oxy)pyridin-3-yl)oxy)methyl)phenyl)propanoate (200 mg) in DMF (5.0 mL) were added 2-fluoro-5-methoxyphenylboronic acid (80 mg), 2.0M aqueous sodium carbonate solution (0.52 mL) and tetrakistriphenylphosphinepalladium (40 mg), and the mixture was stirred at 90° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (27 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6edc410f37624cec97bb4dd687b655bc
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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