Ammonium formate → HCID 10194532, compound

HRID 1295594Notes

Reaction equation

HRID 1295594 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18](=[CH:21][C:22]3[CH:30]=[C:29]4[C:25]([CH2:26][C:27](=[O:31])[NH:28]4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[N:3]=1.C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][C:22]3[CH:30]=[C:29]4[C:25]([CH2:26][C:27](=[O:31])[NH:28]4)=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[N:3]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 10173186HCID 10173186, compound

Product 1

HCID 10194532HCID 10194532, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-{1-[2-(Methylquinolin-5-yloxy)ethyl]piperidin-4-ylidenemethyl}-1,3-dihydroindol-2-one (150 mg; 0.36 mmol) was dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml). Ammonium formate (229 mg; 3.6 mmol) was added, followed by 10% palladium on carbon (150 mg), and the resulting mixture stirred vigorously at ambient temperature for 2 h. The reaction mixture was filtered through Kieselguhr and the filtrate evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with 10% aq. ammoniacal methanol in dichloromethane (5:95), gave the title compound (150 mg; 100%) as a white foam.

Workup

  1. filtrationThe reaction mixture was filtered through Kieselguhr
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. washChromatography on SiO2, eluting with 10% aq. ammoniacal methanol in dichloromethane (5:95)

Sources & evidence

ORD record
ord-e3d307e366964ee8a0c2295725340905
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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