Hydrochloric Acid → 2-[(1-Methyl-1H-indazol-5-yl)oxy]-3-pyridinemethanamine

HRID 2112133Notes

Reaction equation

HRID 2112133 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[N:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[C:13]([CH2:14][NH2:15])=[CH:16][CH:17]=[CH:18][N:19]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574187422-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile

Product 1

HCID 674103932-[(1-Methyl-1H-indazol-5-yl)oxy]-3-pyridinemethanamineYield 35%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

2-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile (3n) (0.132 g, 0.528 mmol) was suspended in MeOH (6 mL). Pd(OH)2 (0.060 mg, 0.427 mmol) was added under a nitrogen atmosphere followed by concentrated aqueous HCl (0.6 mL). The system was purged with H2 gas and the reaction stirred at room temperature for 3 hours under an H2(g) atmosphere. The reaction mixture was filtered through a pad of celite, washed through with MeOH. The organics were concentrated under reduced pressure to afford the crude product, which was purified by flash column chromatography (MeOH/Et3N/EtOAc) to provide the desired product (4n) (0.047 g, 35% yield).

Workup

  1. customThe system was purged with H2 gas
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed through with MeOH
  4. concentrationThe organics were concentrated under reduced pressure
  5. customto afford the crude product, which
  6. customwas purified by flash column chromatography (MeOH/Et3N/EtOAc)

Sources & evidence

ORD record
ord-baf7f7db0d354cd680db8cf2a98125a2
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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