Water → 7-iodo-2-((tetrahydrofuran-2-yl)methyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522585Notes

Reaction equation

HRID 1522585 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[CH2:17][CH2:16][CH2:15][O:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:12][CH:13]3[CH2:17][CH2:16][CH2:15][O:14]3)[N:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 674695597-iodo-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 674695687-iodo-2-((tetrahydrofuran-2-yl)methyl)-2H-pyrazolo[4,3-b]pyridineYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Iodo-1H-pyrazolo[4,3-b]pyridine (50 mg, 0.204 mmol), 2-(bromomethyl)tetrahydrofuran (33.7 mg, 0.204 mmol) and cesium carbonate (133 mg, 0.408 mmol) in DMF (1.0 mL) were heated in a microwave 80° C. for 15 minutes. The reaction was cooled, poured into water (10 mL) and extract with ethyl acetate (5 mL). The organics were dried over sodium sulfate, filtered and concentrated to provide 7-iodo-2-((tetrahydrofuran-2-yl)methyl)-2H-pyrazolo[4,3-b]pyridine (43 mg) which was used as is without further purification. MS [M+H] found 330.1.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextract with ethyl acetate (5 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d491d36231db461b91855eb3fc0797d7
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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