Sodium Bicarbonate → HCID 23295704, compound

HRID 1953971Notes

Reaction equation

HRID 1953971 reaction equation
Br[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:13]=[C:12](C(F)(F)F)[S:11][CH:10]=2)[CH:5]=[C:4]([CH3:18])[CH:3]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(COC)OC.C(OCC)(=O)C.O>[CH3:18][C:4]1[CH:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=2)[N:7]=[C:6]([O:8][C:9]2[CH:13]=[CH:12][S:11][C:10]=2[C:20]([F:31])([F:30])[F:19])[CH:5]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 23295692HCID 23295692, compound

Product 1

HCID 23295704HCID 23295704, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-bromo-4-methyl-2-{[5-(trifluoromethyl)-3-thienyl]oxy}pyridine (1.16 g, 3.43 mmol) in dimethoxyethane is treated with tetrakis(triphenylphosphine) Pd (79 mg, 0.069 mmol), stirred at room temperature for 30 minutes under N2, treated with α,α,α-trifluoro-p-tolylboronic acid (0.72 g, 3.77 mmol), NaHCO3 (0.95 g, 11.32 mmol) and water, heated at reflux temperature for 1.5 hours, cooled to room temperature, diluted with a mixture of ethyl acetate and water to give a two phase mixture. The phases are separated and the organic phase is set aside. The aqueous phase is extracted with ethyl acetate. The ethyl acetate extracts are combined with the organic phase, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give an amber oil residue. The residue is chromatographed (silica gel, ethyl acetate/hexanes, 5/95) to give the title product as a clear oil, which solidified upon drying in a Kugelrohr, to a waxy white solid, 1.22 g (88% yield), mp 52.5-55.5° C., identified by 1HNMR, 13CNMR, 19FNMR, mass spectral and elemental analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1.5 hours
  3. temperaturecooled to room temperature
  4. customto give a two phase mixture
  5. customThe phases are separated
  6. extractionThe aqueous phase is extracted with ethyl acetate
  7. washwashed sequentially with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give an amber oil residue
  11. customThe residue is chromatographed (silica gel, ethyl acetate/hexanes, 5/95)

Sources & evidence

ORD record
ord-8a5081f928884cbb8353a0be7ce510aa
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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