Formic Acid → 4-[4-(4-Fluorophenyl)-1,3-oxazol-5-yl]pyridine

HRID 1454295Notes

Reaction equation

HRID 1454295 reaction equation
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.C(O)=O.C(N(CC)CC)C.[NH2:29][C:30](N)=[O:31]>C(#N)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:29]=[CH:30][O:31][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 1176UreaHCID 8471TriethylamineHCID 111647242-Bromo-1-(4-fluorophenyl)-2-(4-pyridyl)ethanone hydrobromide

Product 1

HCID 166389954-[4-(4-Fluorophenyl)-1,3-oxazol-5-yl]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-bromo-1-(4-fluoro-phenyl)-2-pyridin-4-yl-ethanone hydrobromide (10 g, Reference Example 9) in acetonitrile (100 ml) at 0° C. was treated with formic acid (10 ml) followed by triethylamine (35 ml). The solution was stirred at room temperature for 16 hours and urea (4 g) was added together with formic acid (100 ml). The resulting mixture was refluxed for 6 hours with concomitant removal of the acetonitrile [with a Mc Intire head]. The solvent was then evaporated, the residue taken up into ethyl acetate and the grey solid discarded. The solvent was evaporated and the resulting gum was dissolved in water (100 ml) and the solution basified to pH 11 by addition of sodium hydroxide pellets. The resulting solid was filtered and subjected to flash chromatography on silica eluting with ethyl acetate to give the title compound as a white solid. MS: 241 [MH+]. RF=0.34 (ethyl acetate, determined by thin layer chromatography on silica).

Workup

  1. customThe solvent was then evaporated
  2. customThe solvent was evaporated
  3. dissolutionthe resulting gum was dissolved in water (100 ml)
  4. additionthe solution basified to pH 11 by addition of sodium hydroxide pellets
  5. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-4380901b71a54e699294f186bb8e8513
Source dataset
uspto-grants-2009_01
Patent number
US07479501B2

Reaction notes

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