Tetrahydrofuran → HCID 90403702, compound

HRID 1049253Notes

Reaction equation

HRID 1049253 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=1.C1COCC1>CO.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 90403789HCID 90403789, compound

Product 1

HCID 90403702HCID 90403702, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-methyl-1H-imidazol-1-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (0.73 g, 2.46 mmol) in MeOH (10 mL)/THF (10 mL) was treated with 10% Pd/C (50% wet, 0.261 g, 0.122 mmol) and the mixture was hydrogenated (50 psi) for 16 h at RT. The mixture was filtered through diatomaceous earth and washed with 10% methanol-DCM (3×10 mL). The combined filtrate was concentrated to afford 5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.6 g, 91%) as an off-white solid. MS (ESI) m/z: 268.2 (M+H+).

Workup

  1. customfor 16 h
  2. customat RT
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. washwashed with 10% methanol-DCM (3×10 mL)
  5. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-b40deda897ea4c65816e6f178dc8df63
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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