Water → HCID 67469682, compound

HRID 1522588Notes

Reaction equation

HRID 1522588 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH:13]1([CH2:12][N:10]2[C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[I:1])[CH:8]=[N:9]2)[CH2:15][CH2:14]1.[CH:13]1([CH2:12][N:9]2[CH:8]=[C:4]3[N:5]=[CH:6][CH:7]=[C:2]([I:1])[C:3]3=[N:10]2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503Bromomethylcyclopropane2×HCID 674695597-iodo-1H-pyrazolo[4,3-b]pyridine

Product 2

HCID 67469682HCID 67469682, compoundHCID 674705001-(cyclopropylmethyl)-7-iodo-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-Iodo-1H-pyrazolo[4,3-b]pyridine (50 mg, 0.204 mmol), bromomethylcyclopropane (27.5 mg, 0.204 mmol) and cesium carbonate (133 mg, 0.408 mmol) in DMF (1.0 mL) were heated in a microwave at 80° C. for 15 minutes. Additional bromomethylcyclopropane (27.5 mg, 0.204 mmol) was then added and the reaction was further heated in a microwave at 80° C. for 30 minutes. The reaction was cooled and poured into water (10 mL) and extracted with ethyl acetate (5 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(cyclopropylmethyl)-7-iodo-1H-pyrazolo[4,3-b]pyridine and 2-(cyclopropylmethyl)-7-iodo-2H-pyrazolo[4,3-b]pyridine as a mixture (60/40); MS [M+H] found 300.1.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-939d4880013147b58564dcdaf7e07465
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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