Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 89907301, compound

HRID 526688Notes

Reaction equation

HRID 526688 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH2:26][OH:27])[C:12]([CH3:25])=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1.[H-].[Na+].[CH2:30]([O:32][C:33](=[O:38])[C:34](Br)([CH3:36])[CH3:35])[CH3:31]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:30]([O:32][C:33](=[O:38])[C:34]([O:27][CH2:26][C:11]1[C:12]([CH3:25])=[N:13][C:14]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=2)=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:10]=1)([CH3:36])[CH3:35])[CH3:31]

Participants

6

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 89907741[5-(2,4-Dichloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Product 1

HCID 89907301HCID 89907301, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg of [5-(2,4-Dichloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol in 6 ml of DMF were added 242 mg of sodium hydride (60% in mineral oil) at room temperature. After 15 min, 448 mg of tetrabutylammonium iodide and 946 mg of 2-Bromo-2-methyl-propionic acid ethyl ester were added and the reaction mixture was stirred for 16 h at room temperature. After dilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge by eluting with ethyl acetate The solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 200 mg.

Workup

  1. filtrationAfter dilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate The solvents
  3. customwere removed under reduced pressure
  4. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-5faf061e990b4b6fbe876e69eebfe214
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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