Ammonium formate → HCID 66608590, compound

HRID 1529582Notes

Reaction equation

HRID 1529582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3[N:16]=[C:17](/[CH:19]=[CH:20]/[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:18][C:12]=3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3[N:16]=[C:17]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[O:18][C:12]=3[CH2:11]2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 56941632HCID 56941632, compound

Product 1

HCID 66608590HCID 66608590, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

10% Palladium on charcoal (15 mg, 0.0144 mmol) was added to a stirred suspension of 5-[(4-fluorophenyl)carbonyl]-2-[(E)-2-phenylethenyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (0.05 g, 0.144 mmol) and ammonium formate (54 mg, 0.86 mmol) in MeOH (0.5 mL) in a sealed tube and under nitrogen. The mixture was stirred at 100° C. for 1 hour. The mixture was filtered through a pad of diatomaceous earth and washed with DCM. The filtrate was treated with a saturated solution of sodium chloride and extracted with more DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 5/95). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-[(4-fluorophenyl)carbonyl]-2-(2-phenylethyl)-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine as a colourless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washwashed with DCM
  3. additionThe filtrate was treated with a saturated solution of sodium chloride
  4. extractionextracted with more DCM
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents evaporated in vacuo
  9. customThe crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 5/95)
  10. customThe desired fractions were collected
  11. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-618ffb33f7524385b991c5b428f5e274
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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