Potassium Carbonate → 1-[1-[1-(4-Fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 522320Notes

Reaction equation

Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25]([C:32]#[N:33])=[N:24]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[C:7]([N:4]3[CH2:5][CH2:6][CH:2]([N:23]4[C:27]5=[N:28][CH:29]=[CH:30][CH:31]=[C:26]5[C:25]([C:32]#[N:33])=[N:24]4)[C:3]3=[O:22])[CH:8]=[N:9]2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.080 g, 0.22 mmol), 1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (0.045 g, 0.31 mmol) and K2CO3 (0.070 g, 0.50 mmol) in DMF (2.5 mL) was stirred at 60° C. for 1 hr. It was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution) to give 1-[1-[1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile (0.085 g, 88%).

Workup

temperatureIt was then cooled to room temperature
customquenched with water (30 mL)
extractionextracted with EtOAc (100 mL)
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution)

Sources & evidence

ORD record: ord-6d91d2b9b2734b548a76f83bd4dc0eba
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328116B2

Reaction notes

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