HCID 70981490, compound → HCID 70983946, compound

HRID 1529162Notes

Reaction equation

HRID 1529162 reaction equation
[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9](I)=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cu][C:19]#[N:20]>CS(C)=O.CO>[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([C:19]#[N:20])=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70981490HCID 70981490, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70983946HCID 70983946, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

Under an atmosphere of argon, 6.370 g (purity 83%, 15.447 mmol) of 1-(cyclopentylmethyl)-5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine and 1.522 g (16.992 mmol) of copper(I) cyanide were initially charged in 45 ml of absolute DMSO, and the mixture was heated at 150° C. for 1.5 h. After cooling, the reaction was diluted with methanol and filtered through Celite. The organic phase was washed twice with a mixture of 25% strength aqueous ammonia solution and saturated aqueous ammonium chloride solution (v/v=1:3), then washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. This gave 3.670 g (purity 86%, 97% of theory) of the target compound.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through Celite
  3. washThe organic phase was washed twice with a mixture of 25% strength aqueous ammonia solution and saturated aqueous ammonium chloride solution (v/v=1:3)
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-aa2ad53fc3134572adcad54a142099f5
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

Loading…