Water → HCID 67470499, compound

HRID 1522589

Reaction equation

HRID 1522589 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.Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][C:15]1([CH3:19])[O:14][C@@H:13]([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)[CH2:17][O:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonate3×HCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane3×HCID 67469559HCID 67469559, compound

Product 1

HCID 67470499HCID 67470499, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-Iodo-1H-pyrazolo[4,3-b]pyridine (50 mg, 0.204 mmol), (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (30.7 mg, 0.204 mmol), and cesium carbonate (133 mg, 0.408 mmol) in DMF (1.0 mL) was heated in a microwave at 80° C. for 15 minutes. Additional (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (61.4 mg, 0.204 mmol) and cesium carbonate (67 mg) was added the reaction was heated in microwave at 80° C. for 2 hour. Additional (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (30.7 mg, 0.204 mmol), tetrabutylammonium iodide (301 mg, 0.816 mmol) and cesium carbonate (133 mg, 0.408 mmol) was added and the reaction was heated in microwave at 80° C. for 60 minutes, then the reaction was transferred to an oil bath and heating was continued overnight at 75° C. The reaction was cooled and poured into water (10 mL) and extracted with ethyl acetate (5 mL). The organic layer were dried over sodium sulfate, filtered, and concentrated to give (S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-7-iodo-1H-pyrazolo[4,3-b]pyridine MS [M+H] found 360.2.

Workup

  1. temperaturethe reaction was heated in microwave at 80° C. for 60 minutes
  2. customthe reaction was transferred to an oil bath
  3. temperatureheating
  4. temperatureThe reaction was cooled
  5. extractionextracted with ethyl acetate (5 mL)
  6. dry with materialThe organic layer were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cdcc36c0edf04d7a9763e48de5f857ba
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Linked notes

Loading…