Potassium Iodide → 5-Fluoro-3-iodo-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1615946Notes

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]([F:21])([F:20])[C:14]([F:19])([F:18])[CH2:15][CH2:16]I.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][N:8]([CH2:16][CH2:15][C:14]([F:19])([F:18])[C:13]([F:21])([F:20])[F:12])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

5.0 g (19.010 mmol) of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine were initially charged in DMF (100 ml), and then 20.83 g (76.042 mmol) of 1,1,1,2,2-pentafluoro-4-iodobutane, and also 14.86 g (45.65 mmol) of cesium carbonate and 0.63 g (3.802 mmol) of potassium iodide were added. The mixture was stirred at 140° C. overnight. The mixture was then cooled and combined with a prior experiment which proceeded analogously from 200 mg of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine. Solids were filtered off with suction and washed with DMF, and then the liquid was concentrated under high vacuum. The residue was purified by means of preparative HPLC (methanol:water gradient). This gave 4.34 g (52% of theory) of the title compound in solid form.

Workup

temperatureThe mixture was then cooled
filtrationSolids were filtered off with suction
washwashed with DMF
concentrationthe liquid was concentrated under high vacuum
customThe residue was purified by means of preparative HPLC (methanol:water gradient)

Sources & evidence

ORD record: ord-5dc19564956b43209b95a159211e79d7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765769B2

Reaction notes

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