Water → 5-Fluoro-1-[(3-fluoropyridin-2-yl)methyl]-3-iodo-1H-pyrazolo[3,4-b]pyridine

HRID 536483Notes

Reaction equation

HRID 536483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=1.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][N:8]([CH2:19][C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=3)[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 216131732-(Bromomethyl)-3-fluoropyridineHCID 178505979HCID 178505979, compound

Product 1

HCID 711874705-Fluoro-1-[(3-fluoropyridin-2-yl)methyl]-3-iodo-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6.291 g (23.921 mmol) of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine and 8.573 g (26.313 mmol) of caesium carbonate were put in DMF (10 ml) and then 5.00 g (26.313 mmol) of 2-(bromomethyl)-3-fluoropyridine dissolved in DMF (20 ml) was added dropwise. The mixture was stirred overnight at RT. Then it was left to cool and was poured into 200 ml water. A precipitate was filtered off with suction, it was washed with water and dried overnight under high vacuum. 6.28 g (70% of theor.) of the title compound was obtained.

Workup

  1. additionwas added dropwise
  2. waitThen it was left
  3. temperatureto cool
  4. filtrationA precipitate was filtered off with suction, it
  5. washwas washed with water
  6. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-80279174063a4dc68f48bdf233535389
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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