HCID 90403618, compound → HCID 90403314, compound

HRID 2278901Notes

Reaction equation

HRID 2278901 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:28]([O-])=O)[N:3]=1>CO.[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([NH2:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 90403618HCID 90403618, compound

Product 1

HCID 90403314HCID 90403314, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)-6-nitropyridine (0.553 g, 1.367 mmol) in MeOH (20 mL) was treated with 10% Pd/C (50% w/w water, 146 mg, 0.137 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration, washed with MeOH and the filtrate concentrated to dryness to afford 6-methyl-5-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)pyridin-2-amine (446 mg, 87%). MS (ESI) m/z: 375.2 (M+H+).

Workup

  1. customThe solids were removed via filtration
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-dce7c21d9a3344358ded45457dd23ad8
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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