Ammonium formate → HCID 89666803, compound

HRID 2171243Notes

Reaction equation

HRID 2171243 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)[C:9]([F:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:19]1[N:28]=[C:27]([N:29]2[CH:33]=[CH:32][N:31]=[N:30]2)[C:26]([F:34])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C([O-])=O.[NH4+]>CO.[Pd]>[F:17][C:9]1[C:10]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[N:11][CH:2]=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5].[F:34][C:26]1[C:27]([N:29]2[CH:33]=[CH:32][N:31]=[N:30]2)=[N:28][CH:19]=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 3

HCID 2723923Ammonium formateHCID 89666798HCID 89666798, compoundHCID 89666799HCID 89666799, compound

Product 2

HCID 89666803HCID 89666803, compoundHCID 89666838HCID 89666838, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of methyl 2-chloro-5-fluoro-6-(2H-1,2,3-triazol-2-yl)nicotinate and methyl 2-chloro-5-fluoro-6-(1H-1,2,3-triazol-1-yl)nicotinate obtained in the 1st step was dissolved in MeOH (5 ml) and ammonium formate (300 mg) and 10% Pd/C (200 mg) were added thereto, followed by reflux for 4.5 hours. The reaction solution was adjusted to room temperature and filtered through Celite, the filtrate was collected, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1). A white solid of methyl 5-fluoro-6-(2H-1,2,3-triazol-2-yl)nicotinate (250 mg) and a white solid of methyl 5-fluoro-6-(1H-1,2,3-triazol-1-yl)nicotinate (160 mg) were thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureby reflux for 4.5 hours
  3. customwas adjusted to room temperature
  4. filtrationfiltered through Celite
  5. customthe filtrate was collected
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record
ord-7b689598920245cb9f8795d85069b6d7
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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