Ammonium formate → 9-(1-Acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methyl-pyrimidin-5-yl)-nonanoic acid ethyl ester

HRID 2120701Notes

Reaction equation

HRID 2120701 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]([C:25]1[CH:26]=[N:27][C:28]([CH3:31])=[N:29][CH:30]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]=[C:17]2[N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:16]2=[CH:15][CH:14]=1)[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]([C:25]1[CH:26]=[N:27][C:28]([CH3:31])=[N:29][CH:30]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]=[C:17]2[N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21][C:16]2=[CH:15][CH:14]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 696665499-(1-Acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methyl-pyrimidin-5-yl)-non-4-enoic acid ethyl ester

Product 1

HCID 587655219-(1-Acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methyl-pyrimidin-5-yl)-nonanoic acid ethyl esterYield 33.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 23-10 (0.150 g, 0.34 mmol), ammonium formate (0.192 g, 3.09 mmol), and 10% Pd/C (0.150 g) in EtOH (25 mL) was refluxed for 15 minutes. Filtration through celite and evaporative removal of the solvent followed by purification by PCTLC (0-10% MeOH-CHCl3) afforded 0.050 g of 23-11.

Workup

  1. filtrationFiltration through celite
  2. customremoval of the solvent
  3. customfollowed by purification by PCTLC (0-10% MeOH-CHCl3)

Sources & evidence

ORD record
ord-31a790bc57ad44de9ced6fefb25b7e37
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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