Sodium Bicarbonate → 3-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehyde

HRID 1923599Notes

Reaction equation

HRID 1923599 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH:13]=[O:14])=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66643813[3-(5-Fluoro-pyridin-2-yl)-isoxazol-4-yl]-methanol

Product 1

HCID 866472733-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehydeYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of [3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-methanol (2.1 g, 10.8 mmol) in DCM (45 mL) was added a suspension of DMP (5.5 g, 13.0 mmol) in DCM (35 mL) portionwise and under Argon at room temperature and then the mixture was cooled to 0° C. and the resulting mixture warmed up to room temperature overnight. The mixture was then poured carefully into stirred saturated sodium hydrogen carbonate solution and the aqueous layer extracted with DCM. The combined organic layers were then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) gave the title compound (1.85 g, 89%) as a white solid. MS: m/e=193.1 [M+H]+.

Workup

  1. temperaturethe resulting mixture warmed up to room temperature overnight
  2. additionThe mixture was then poured carefully
  3. extractionthe aqueous layer extracted with DCM
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2b091751b08a4b53ab42676a4f0bef74
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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