Ammonium formate → HCID 57633117, compound

HRID 2108763Notes

Reaction equation

HRID 2108763 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57633126HCID 57633126, compound

Product 1

HCID 57633117HCID 57633117, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Nitro-phenyl)-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide (1 g, 2.6 mmol) was dissolved in MeOH (100 ml) and added 10% Pd/C (100 mg) followed by ammonium formate (3eq, 500 mg). The reaction mixture was refluxed overnight. Then the reaction mixture was filtered and concentrated to give a white solid. The solid was taken up in EtOAc, filtered again, concentrated to give white solid. (500 mg, 55% yield).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationThen the reaction mixture was filtered
  3. concentrationconcentrated
  4. customto give a white solid
  5. filtrationfiltered again
  6. concentrationconcentrated
  7. customto give white solid

Sources & evidence

ORD record
ord-bbd638d5d3bb457093f0a213a346ff10
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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