HCID 90403318, compound → HCID 90403398, compound

HRID 1049262Notes

Reaction equation

HRID 1049262 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]3)[CH:10]=2)=[CH:6][N:5]=[C:4]([N+:21]([O-])=O)[CH:3]=1>CO.C1COCC1.[Pd]>[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]3)[CH:10]=2)=[CH:6][N:5]=[C:4]([NH2:21])[CH:3]=1

Participants

5

Reactant 1

HCID 90403318HCID 90403318, compound

Product 1

HCID 90403398HCID 90403398, compoundYield 77.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)-2-nitropyridine (2.5 g, 8.03 mmol) in MeOH (40 mL) and THF (20 mL) was treated with 10% Pd/C (50% w/w water, 0.855 g, 0.8 mmol) and hydrogenated (50 psi) for 24 h. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness. The residue was stirred with 60% EtOAc/Hex for 15 min. The suspension was collected by filtration, washed with 60% EtOAc/Hex, and dried in vacuo to afford 4-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-amine (1.75 g, 77%). 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J=1.3 Hz, 1H), 8.27 (d, J=5.8 Hz, 1H), 7.72 (s, 1H), 7.62 (s, 1H), 7.30 (d, J=2.2 Hz, 1H), 6.62 (dd, J=5.8, 2.2 Hz, 1H), 6.39 (s, 1H), 5.94 (s, 2H), 2.13 (s, 3H), 1.96 (s, 3H); MS (ESI) m/z: 282.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated to dryness
  4. filtrationThe suspension was collected by filtration
  5. washwashed with 60% EtOAc/Hex
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a0e7a2019c0442e1b8638242d7cefd0d
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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