Methyl iodide → 4-bromo-1-(2-methoxy-ethyl)-1H-pyrazolo[3,4-c]pyridine

HRID 446920Notes

Reaction equation

HRID 446920 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH2:11][CH2:12][OH:13])[N:9]=[CH:10][C:3]=12.[H-].[Na+].[CH3:16]I>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH2:11][CH2:12][O:13][CH3:16])[N:9]=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576067822-(4-Bromo-pyrazolo[3,4-c]pyridin-1-yl)-ethanol2×

Product 1

HCID 576067944-bromo-1-(2-methoxy-ethyl)-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 675 mg of 2-(4-bromo-pyrazolo[3,4-c]pyridin-1-yl)-ethanol (Intermediate 2.2; 2.79 mmol, 1 eq.) in 33 mL THF was treated at rt with 183 mg sodium hydride (55-60% suspension; 4.18 mmol, 1.5 eq.) and stirred for 30 min upon which 0.194 mL methyl iodide (3.07 mmol, 1.1 eq.) were added and stirring was continued for 2 h. The reaction mixture was quenched with water, extracted with ethyl acetate, the combined organic layers were dried and concentrated in vacuo. Flash column chromatography provided 500 mg of the corresponding methyl ether target compound (1.95 mmol, 70% yield).

Workup

  1. additionwere added
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customthe combined organic layers were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-247867cd1dc9431bb7183698468bf6dd
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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