Hydrochloric Acid → HCID 23295692, compound

HRID 1953970Notes

Reaction equation

HRID 1953970 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](F)[N:3]=1.[OH:10][C:11]1[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[S:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([O:10][C:11]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[S:14][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 110842734-Hydroxy-2-(trifluoromethyl)thiopheneHCID 299193662-Bromo-6-fluoro-4-methylpyridine

Product 1

HCID 23295692HCID 23295692, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromo-6-fluoro-4-methyipyridine (1.00 g, 5.26 mmol) and 4-hydroxy-2-(trifluoromethyl)-thiophene (0.88 g, 5.26 mmol) in dimethylformamide is treated with K2CO3 (1.09 g, 7.89 mmol), heated at 80° C. for 23 hours, cooled to room temperature, poured onto water, acidified to pH 5-6 with 6N HCl and extracted with ether. The ether extracts are combined, washed sequentially with water and brine, dried over MgSQ4 and concentrated in vacuo to give a residue. The residue is chromatographed (silica gel, ethyl acetate/hexanes, 3/97) to afford the title produce as a yellow oil, 1.16 g (65% yield), identified by 1HNMR and 19FNMR analyses.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto water
  3. extractionextracted with ether
  4. washwashed sequentially with water and brine
  5. customdried over MgSQ4
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is chromatographed (silica gel, ethyl acetate/hexanes, 3/97)
  9. customto afford the title
  10. customproduce as a yellow oil, 1.16 g (65% yield)

Sources & evidence

ORD record
ord-68c94b13b7ba4a94acd92a7c5a0e42c7
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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