Anisole → 6-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine

HRID 57828Notes

Reaction equation

HRID 57828 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17](COCC[Si](C)(C)C)[C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2].C1(OC)C=CC=CC=1.O1CCOCC1>Cl>[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][NH:17][C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 312751,4-DioxaneHCID 867070332-[[6-(5-Ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl-trimethyl-silane

Product 1

HCID 867070346-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridineYield 174.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-[[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl-trimethyl-silane (0.2456 mmol; 106.8 mg) and anisole (1.228 mmol; 133 mg; 0.134 ml) in hydrogen chloride, 4.0 M in 1,4-dioxane (20 mmol; 5 ml) was stirred at room temperature overnight. The mixture was concentrated to afford 6-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine (˜95.9 mg), which was used without purification.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-96f707140a3f498083b7d2e34fcf2110
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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