Ammonium formate → 6-(1-Methylpiperidin-4-yl)-4-(propan-2-yloxy)pyridin-3-amine

HRID 518828Notes

Reaction equation

HRID 518828 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[C:11]([N+:18]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:18])=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 866979932-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitro-4-propan-2-yloxypyridine

Product 1

HCID 866979946-(1-Methylpiperidin-4-yl)-4-(propan-2-yloxy)pyridin-3-amineYield 105.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In a microwave tube, 400 mg of 1′-methyl-5-nitro-4-(propan-2-yloxy)-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine are introduced into 30 ml of methanol. 546 mg of ammonium formate and 333 mg of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure, so as to give 380 mg of 6-(1-methylpiperidin-4-yl)-4-(propan-2-yloxy)pyridin-3-amine in the form of a brown oil.

Workup

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7389b52fd7d444e848ae7d93618815a
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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