5-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide → HCID 178485250, compound

HRID 219384Notes

Reaction equation

HRID 219384 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]([NH:20][CH3:21])=[O:19])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[O:15][C:12]2=[CH:13][N:14]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:16]2[O:15][C:12]3=[CH:13][N:14]=[C:9]([OH:8])[CH:10]=[C:11]3[C:17]=2[C:18]([NH:20][CH3:21])=[O:19])=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 672175935-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide

Product 1

HCID 178485250HCID 178485250, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (178 mg, 0.084 mmol) (10%; 50% wet) was added to a stirring solution of 5-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide (630 mg, 1.674 mmol) in THF (83 ml) at room temperature. It was placed under an atmosphere of H2 and allowed to stir for 20 minutes after which a precipitate had formed. The reaction was purged with N2 and diluted with MeOH until all solids had dissolved. The mixture was filtered through a pad of celite washing with MeOH and the filtrate was concentrated to give the expected product 2-(4-fluorophenyl)-5-hydroxy-N-methylfuro[2,3-c]pyridine-3-carboxamide (460 mg, 1.53 mmol, 91% yield) consistent by LCMS and NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.30-8.40 (2H, m), 7.98 (2H, dd, J=8.78, 5.77 Hz), 7.35-7.45 (3H, m), 6.61 (1H, s), 2.81 (3H, d, J=4.52 Hz). LC-MS retention time: 0.847 min; m/z (MH+): 287. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. customhad formed
  2. customThe reaction was purged with N2
  3. additiondiluted with MeOH until all solids
  4. dissolutionhad dissolved
  5. filtrationThe mixture was filtered through a pad of celite
  6. washwashing with MeOH
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6dc93860edf84594b32156050c8b5536
Source dataset
uspto-grants-2012_06
Patent number
US08198449B2

Reaction notes

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