HCID 66731691, compound → HCID 66732517, compound

HRID 1963162Notes

Reaction equation

HRID 1963162 reaction equation
[ClH:1].[F:2][C:3]([F:21])([F:20])[C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1>CO.[Pt](=O)=O>[ClH:1].[F:21][C:3]([F:2])([F:20])[C:4]1[N:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 66731691HCID 66731691, compound

Product 1

HCID 66732517HCID 66732517, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 6′-(trifluoromethyl)-2,3′-bipyridine-4-carboxylate hydrochloride (2.5 g, 7.86 mmol) was dissolved in MeOH (20 mL) and platinum(IV) oxide (0.036 g, 0.16 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1 h. Additional catalyst was added and the hydrogenation was continued for 1 h. The catalyst was filtered off, washed with MeOH and the eluate evaporated yielding methyl 2-(6-(trifluoromethyl)pyridin-3-yl)piperidine-4-carboxylate hydrochloride (2.2 g, 86%) as a brown solid. MS m/z 289 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. additionAdditional catalyst was added
  3. waitthe hydrogenation was continued for 1 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with MeOH
  6. customthe eluate evaporated

Sources & evidence

ORD record
ord-1838349bcf8547339cfe106510b87d88
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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