N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide → N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)isobutyramide

HRID 626550Notes

Reaction equation

HRID 626550 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:21]([O-])=O)[N:3]=1>[Pd].CCOC(C)=O.CO>[NH2:21][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 90410828N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide

Product 1

HCID 90409610N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)isobutyramideYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (0.55 g, 1.739 mmol) in 2:1 EtOAc/MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.206 g, 0.174 mmol) and hydrogenated (1 atm) for 2 days. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate was concentrated to dryness to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (410 mg, 82%). 1H NMR (400 MHz, DMSO-d6): δ 10.41 (s, 1H), 8.12 (d, J=5.7 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.16 (d, J=8.7 Hz, 1H), 6.58 (dd, J=5.7, 2.4 Hz, 1H), 6.35 (d, J=8.7 Hz, 1H), 5.95 (s, 2H), 2.69 (m, 1H), 2.04 (s, 3H), 1.02 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 287.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-56abcc845b354da88531e3b0cc1df5b4
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

Loading…