Ammonium formate → HCID 68428543, compound

HRID 642409Notes

Reaction equation

HRID 642409 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16](Cl)=[C:15](Cl)[N:14]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68428125HCID 68428125, compound

Product 1

HCID 68428543HCID 68428543, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 7-cyano-2,3-dichloro-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (0.66 g, 1.78 mmol), example 96(f), and ammonium formate (2.25 g, 35.7 mmol) in 62 mL of ethyl acetate was added 10 wt. % palladium on carbon (312 mg). The reaction mixture was refluxed for 1 h. The catalyst was filtered off, and the filtrate was concentrated to afford 0.48 g of a white solid. MS: (+) m/z 302.3 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e1988e0d8ca64bee90448a72544b2407
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…