HCID 67367246, compound → HCID 67367265, compound

HRID 1895758Notes

Reaction equation

HRID 1895758 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=2[F:23])[C:11](=[O:24])[CH:10]=1)C1C=CC=CC=1>[Pd].CO>[F:23][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:15]=1[N:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]1=[O:24])[C:19]#[N:20]

Participants

4

Reactant 1

HCID 67367246HCID 67367246, compound

Product 1

HCID 67367265HCID 67367265, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-fluorobenzonitrile (250 mg, 0.780 mmol) and 10% palladium on carbon (50 mg, 0.470 mmol) was applied vacuum then placed under an atmosphere of nitrogen. Methanol (5 mL)was added and vacuum applied briefly. The reaction was placed under an atmosphere of hydrogen for 6 hours. The reaction mixture was passed through a 10×10 mm CELITE® 545 filter aid plug eluting with an additional 10 mL each of MeOH and CH2Cl2. The filtrate was concentrated to 170 mg of a pale tan foam. Added 5 mL MeOH and heated to reflux, filtered hot and rinsed with 3×2 mL warm MeOH. The filtrate was concentrated to crude product (166 mg, 0.577 mmol, 74%) as a pale yellow solid which was used as obtained in the subsequent step. MS (ESI) 231.1 (M+1).

Workup

  1. filtrationfilter aid plug
  2. washeluting with an additional 10 mL each of MeOH and CH2Cl2
  3. concentrationThe filtrate was concentrated to 170 mg of a pale tan foam
  4. additionAdded 5 mL MeOH
  5. temperatureheated
  6. temperatureto reflux
  7. filtrationfiltered hot
  8. washrinsed with 3×2 mL
  9. temperaturewarm MeOH
  10. customas obtained in the subsequent step

Sources & evidence

ORD record
ord-f58b43a95a424f24b2cf5ed9e423c638
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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