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

HRID 1529157Notes

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 had been carried out analogously using 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 filtrate 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.

Workup

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

Sources & evidence

ORD record: ord-7cfa3e0b6ef4449a8fe6c2bb1a647432
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090610B2

Reaction notes

Loading…