Methyl iodide → 3-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine

HRID 246565

Reaction equation

HRID 246565 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH3:11]C(C)([O-])C.[K+].IC>C1COCC1.O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178506575HCID 178506575, compound

Product 1

HCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridineYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-iodo-1H-pyrazolo[3,4-b]pyridine (3.5 g, 14.3 mmol) in THF (70 mL) at 0° C. was added potassium tert-butoxide (1.92 g, 17.1 mmol) and the reaction mixture stirred at 0° C. for 1 h. Iodomethane (2.43 g, 1.07 mL, 17.1 mmol) was added drop-wise, then the mixture was warmed to rt. After 6 h the mixture was diluted with water, extracted with dichloromethane, then the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 20-60% ethyl acetate in hexanes) gave 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (1.14 g, 4.4 mmol, 31%) as an off-white solid. MS (M+H)+=260.

Workup

  1. temperaturethe mixture was warmed to rt
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (silica, 20-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-750f9ba1df90465aaebfddd99af7669b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

Loading…