7-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-3-nitropyrazolo[1,5-a]pyridine → 7-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-2-ethylpyrazolo[1,5-a]pyridine-3-amine

HRID 2253412Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:19]2[N:20]=[C:21]([CH2:26][CH3:27])[C:22]([N+:23]([O-])=O)=[C:18]2[CH:17]=[CH:16][CH:15]=1>[C].[Pd].CO>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:14]1[N:19]2[N:20]=[C:21]([CH2:26][CH3:27])[C:22]([NH2:23])=[C:18]2[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (850 mg, 2.3 mmol), 10% palladium-carbon (50% wet, 330 mg) and methanol (19 mL) was stirred for 13 hours at 50° C. under a hydrogen atmosphere at atmospheric pressure. After cooling the reaction mixture to room temperature, the reaction mixture was filtered through celite to remove the catalyst. The solvent of the obtained filtrate was evaporated under reduced pressure to afford 3.45 g of the title compound (84% yield).

Workup

temperatureAfter cooling the reaction mixture to room temperature
filtrationthe reaction mixture was filtered through celite
customto remove the catalyst
customThe solvent of the obtained filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c44aa74ad8a44b619b0fe6b5ce1fa549
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323569B2

Reaction notes

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