Dimethylformamide → 1-{2-[4-(4-Chloro-2-fluoro-5-methoxy-phenyl)-2-(S)-methyl-piperazin-1-yl]-2-oxo-ethyl}-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 503875Notes

Reaction equation

HRID 503875 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[CH2:17][N:18]3[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[C:20](I)=[N:19]3)[C@@H:12]([CH3:29])[CH2:11]2)=[C:4]([F:30])[CH:3]=1.[C:31]([Cu])#[N:32].CN(C=O)C>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[CH2:17][N:18]3[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[C:20]([C:31]#[N:32])=[N:19]3)[C@@H:12]([CH3:29])[CH2:11]2)=[C:4]([F:30])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 160060321-[(S)-4-(4-Chloro-2-fluoro-5-methoxy-phenyl)-2-methyl-piperazin-1-yl]-2-(3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-ethanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 576427861-{2-[4-(4-Chloro-2-fluoro-5-methoxy-phenyl)-2-(S)-methyl-piperazin-1-yl]-2-oxo-ethyl}-1H-pyrazolo[3,4-b]pyridine-3-carbonitrileYield 0%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 1-[(S)-4-(4-Chloro-2-fluoro-5-methoxy-phenyl)-2-methyl-piperazin-1-yl]-2-(3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-ethanone (2.2 g, 4.0 Mmol, 1 eq), CuCN (3.6 g, 40 Mmol, 10 eq), and DMF (25 mL) was stirred at 175° C. for 1 hrs. The reaction mixture was cooled to rt, diluted with ethyl acetate and filtered. The filtrate was washed with water, dried over Na2SO4, and purified by flash chromatography to provide 1-{2-[4-(4-Chloro-2-fluoro-5-methoxy-phenyl)-2-(S)-methyl-piperazin-1-yl]-2-oxo-ethyl}-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (1.6 g).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. dry with materialdried over Na2SO4
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2f71f7d84fee40bb90ac5d9cdc834891
Source dataset
uspto-grants-2010_08
Patent number
US07777035B2

Reaction notes

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