Ammonium formate → HCID 18926564, compound

HRID 1600185Notes

Reaction equation

HRID 1600185 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:13][CH:14]=2)[C:9]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:8]1)=[O:4].C([O-])=O.[NH4+]>[Pd].CO.O1CCCC1>[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:13][CH:14]=2)[C:9]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:8]1)=[O:4]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86752488HCID 86752488, compound

Product 1

HCID 18926564HCID 18926564, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of t-butyl (E)-3-[1-(2-methoxycarbonylethyl)-3-(3-pyridylmethyl)-1H-indol-5-yl]-2-propenoate (7.86 g), 10% palladium on carbon (0.70 g) and ammonium formate (5.60 g) in a mixture of methanol (40 ml) and tetrahydrofuran (40 ml) was heated at 60° C. for 3 hours and then cooled. The mixture was filtered and the residue was washed with methanol. The filtrate and washings were combined and evaporated, and the residue-was partitioned between water and ether. The organic layer was separated and the aqueous layer was extracted with ether. The organic layers were combined, washed with water and dried (MgSO4). Evaporation of the solvent gave the title compound as an oil (7.80 g). Found: C,70.51; H,6.98; N,6.54. C25H30N2O4 requires: C,71.06; H,7.16; N,6.63%.

Workup

  1. temperaturecooled
  2. filtrationThe mixture was filtered
  3. washthe residue was washed with methanol
  4. customevaporated
  5. customthe residue-was partitioned between water and ether
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ether
  8. washwashed with water
  9. dry with materialdried (MgSO4)
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-af49b6779c4f4d9393e39a3016248129
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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