2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester → Methyl Benzoate

HRID 1515829Notes

Reaction equation

HRID 1515829 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7](C(C2NC3=NC=C(F)C=C3C=2)=CC2CCOCC2)=[CH:6][C:5]=1F>[Pd].CO>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 672294732-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester

Product 1

HCID 7150Methyl BenzoateYield 268.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester (250 mg, 0.63 mmol) and 10% palladium on activated carbon (75 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo to afford 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethyl]-ethyl]-benzoic acid methyl ester (230 mg, 91%) which was used in the next step without further purification: LC/MS m/e calcd for C22H22F2N2O3 [M+H]+ 401.43, observed 400.9.

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. filtrationthe solids filtered off
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35c9729de521434592040e914f91e527
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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