Water → 5-Fluoro-3-iodo-1-(2,3,6-trifluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1505462Notes

Reaction equation

HRID 1505462 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.[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[C:17]([F:22])[C:14]=1[CH2:15]Br.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][N:8]([CH2:15][C:14]3[C:17]([F:22])=[CH:18][CH:19]=[C:20]([F:21])[C:13]=3[F:12])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5190612,3,6-Trifluorobenzyl bromideHCID 178505979HCID 178505979, compound

Product 1

HCID 666561625-Fluoro-3-iodo-1-(2,3,6-trifluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g (38.021 mmol) of the compound from Example 6A were initially charged in DMF (170 ml), and 9.41 g (41.823 mmol) of 2,3,6-trifluorobenzyl bromide and 13.62 g (41.82 mmol) of caesium carbonate were then added. The mixture was stirred at RT overnight. The reaction mixture was then added to water (200 ml) and stirred for 15 min A precipitate was filtered off with suction, washed with water and subsequently dried under high vacuum. This gave 12.1 g of the title compound (78% of theory).

Workup

  1. stirringstirred for 15 min A precipitate
  2. filtrationwas filtered off with suction
  3. washwashed with water
  4. customsubsequently dried under high vacuum

Sources & evidence

ORD record
ord-509d7d7548c64cc4b4210fdb36f466e6
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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