Ammonium formate → HCID 57863442, compound

HRID 1446755Notes

Reaction equation

HRID 1446755 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=1)=[O:27])([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19]4[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=4)=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([C:35]([F:36])([F:38])[F:37])[CH:32]=[CH:31][N:30]=1)=[O:27]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68548276HCID 68548276, compound

Product 1

HCID 57863442HCID 57863442, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Suspend 2-[2-nitro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(4-trifluoromethyl-pyridin-2-yl)-acetamide (0.18 g, 0.35 mmol) and ammonium formate (0.11 g, 1.82 mmol) in anhydrous methanol (5 mL) and bubble nitrogen through the solution for 5 minutes. Under a positive stream of nitrogen, add 10% Pd-on carbon (0.03, 0.03 mmol) to the solution and stir the reaction at ambient temperature for 18 hours. Filter the reaction contents through a pad of Celite® and wash the pad with methanol (40 mL). Concentrate the solution and then chromatograph the residue on silica using a gradient of (0→2→5%) methanol in dichloromethane to yield the title compound (0.03 g, 0.05 mmol). MS(ES), m/z 489 (M+1).

Workup

  1. custombubble nitrogen through the solution for 5 minutes
  2. customthe reaction at ambient temperature for 18 hours
  3. filtrationFilter
  4. customthe reaction contents through a pad of Celite®
  5. washwash the pad with methanol (40 mL)
  6. concentrationConcentrate the solution

Sources & evidence

ORD record
ord-137ac95a086d4245af0645ef4ae250d1
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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