Dimethylformamide → HCID 68040977, compound

HRID 710612Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.F[C:12]1[C:13]([CH:18]=O)=[N:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:12]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:18]=[N:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a 500-mL round-bottomed flask was added 4-fluorophenylhydrazine hydrochloride (18.9 g, 116 mmol), 3-fluoro-2-formylpyridine (14.2 g, 113 mmol), K2CO3 (47.0 g, 340 mmol), and DMF (150 mL). The slurry was heated to 120° C. in an oil bath for 41 hours at which point the reaction mixture was cooled and poured into 1.2 L of H2O. The tan precipitate was collected via vacuum filtration and washed with 3×H2O. The solid was dissolved in CH2Cl2 and the resulting solution was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The solid was triturated with 200 mL of 9:1 hexanes:EtOAc and dried to provide 1-(4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridine (16.3 g, 68%) as a tan powder. MS: (ES) m/z calculated for C12H9FN3 [M+H]+ 214.1, found 214.1.

Workup

temperaturewas cooled
filtrationThe tan precipitate was collected via vacuum filtration
washwashed with 3×H2O
dissolutionThe solid was dissolved in CH2Cl2
washthe resulting solution was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a brown solid
customThe solid was triturated with 200 mL of 9:1 hexanes
dry with materialEtOAc and dried

Sources & evidence

ORD record: ord-9f35183ca74d47098f1c06ae32f88657
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Reaction notes

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