Cesium carbonate → HCID 131734932, compound

HRID 921576Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[N+:30]([O-:32])=[O:31].[Cl-].[NH4+]>C(#N)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:24]3[C:23]([N+:30]([O-:32])=[O:31])=[CH:22][CH:29]=[CH:28][C:25]=3[C:26]#[N:27])[N:9]=[C:10]([C:11]([F:14])([F:12])[F:13])[C:3]=12

Participants

Conditions

Temperature: 70 °C

Procedure

Compound (153a) (5.00 g), cesium carbonate (6.72 g), and 4-chloro-3-nitrobenzonitrile (3.21 g) were suspended in acetonitrile (50 mL), followed by stirring at 70° C. for 4 hr. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the precipitate was collected by filtration and dried under reduced pressure to obtain 4-{(4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g, 98%). The obtained 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g) was suspended in THF (50 mL), MeOH (50 mL), and water (50 mL), and ammonium chloride (7.20 g) and iron powder (8.76 g) were added to the resulting suspension, followed by stirring at 80° C. for 2 hr. The reaction solution was diluted with ethyl acetate, and insoluble matters were filtered by celite. The solvent of the filtrate was distilled away, and water was added to the residue. Insoluble matters were collected by filtration and dried under reduced pressure to obtain compound (158a) (6.44 g, 96%).

Workup

filtrationthe precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-a10cb9f4f43b497696dfef6be615cf83
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273045B2

Reaction notes

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