Methanol → HCID 67500719, compound

HRID 1625265Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=3[N+:23]([O-])=O)[N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.CO.O.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C.[Fe]>[NH2:23][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:15]=1[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([I:1])=[C:3]2[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9]1)[C:19]#[N:20]

Participants

Conditions

Temperature: 80 °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

filtrationwere filtered by celite
distillationThe solvent of the filtrate was distilled away
additionwater was added to the residue
filtrationInsoluble matters were collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-b66550610b4148c3966c8276b2dff6f7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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