Ammonium Chloride → HCID 90403702, compound

HRID 2278909Notes

Reaction equation

HRID 2278909 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.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[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

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90403789HCID 90403789, compound

Product 1

HCID 90403702HCID 90403702, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(4-methyl-1H-imidazol-1-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (1.3 g, 4.37 mmol) in MeOH (20 mL)/THF (20 mL) was treated sequentially with NH4Cl (7.02 g, 131 mmol) and zinc dust (2.86 g, 43.7 mmol) and stirred at RT for 2 h. The mixture was diluted with THF, the solids removed via filtration through diatomaceous earth, washed with THF and the filtrate concentrated to dryness. The material was treated with THF, the solids removed via filtration and the filtrate concentrated to dryness, treated with DCM and sonicated. The resulting solid was collected via filtration and dried to afford 5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-amine (800 mg, 68%). 1H NMR (400 MHz, DMSO-d6): δ 8.39 (d, J=1.4 Hz, 1 H), 8.28 (d, J=5.8 Hz, 1 H), 7.83 (d, J=2.9 Hz, 1 H), 7.63 (s, 1 H), 7.31-7.30 (m, 2 H), 6.70 (dd, J=5.8, 2.2 Hz, 1 H), 6.51 (d, J=8.9 Hz, 1 H), 6.05 (s, 2 H), 2.14 (d, J=1.0 Hz, 3 H); MS (ESI) m/z: 268.2 (M+H+).

Workup

  1. customthe solids removed via filtration through diatomaceous earth
  2. washwashed with THF
  3. concentrationthe filtrate concentrated to dryness
  4. additionThe material was treated with THF
  5. customthe solids removed via filtration
  6. concentrationthe filtrate concentrated to dryness
  7. additiontreated with DCM
  8. customsonicated
  9. filtrationThe resulting solid was collected via filtration
  10. customdried

Sources & evidence

ORD record
ord-0a437cad6f844605a2dad628a640495d
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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