Potassium Cyanide → HCID 69093841, compound

HRID 2174269Notes

Reaction equation

Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:3]=1.[C-:21]#[N:22].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][N:6]1[C:2]([C:21]#[N:22])=[N:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(5-bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16, e.g., about 0.95 g, 2.9 mmol) in N,N-dimethylformamide (e.g., 9.5 mL) is added potassium cyanide (e.g., about 0.928 g, 14.3 mmol). After heating the solution at about 100° C. for about 22 h, the solution is diluted with ethyl acetate (e.g., about 125 mL) and water (e.g., about 100 mL). The layers are separated, and the aqueous layer is extracted with ethyl acetate (e.g., about 2×50 mL). The organics are combined, washed with water (e.g., about 50 mL) and brine (e.g., about 50 mL), dried, e.g., over sodium sulfate or magnesium sulfate, filtered, and the solvent is removed in vacuo to give the crude product, I-33. Purification by silica gel chromatography (0-15% ethyl acetate in dichloromethane) yields 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carbonitrile I-33 (I-33) as a solid.

Workup

customThe layers are separated
extractionthe aqueous layer is extracted with ethyl acetate (e.g., about 2×50 mL)
washwashed with water (e.g., about 50 mL) and brine (e.g., about 50 mL)
customdried
filtratione.g., over sodium sulfate or magnesium sulfate, filtered
customthe solvent is removed in vacuo
customto give the crude product
customPurification by silica gel chromatography (0-15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-0d3643dbca294ec5bc3f52dcdf15bf22
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061030B2

Reaction notes

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