Water → HCID 86677487, compound

HRID 1621134Notes

Reaction equation

Br[CH2:2][C:3]1[C:7]([CH3:8])=[CH:6][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1.[C-:15]#[N:16].[K+].O>CS(C)=O>[CH3:8][C:7]1[C:3]([CH2:2][C:15]#[N:16])=[N:4][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-(bromomethyl)-4-methyl-1-phenyl-1H-pyrazole (112 mg, 446 μmol) and potassium cyanide (33.3 mg, 491 μmol) in DMSO (2 mL) was heated to 60° C. for 2 h. The reaction mixture was cooled to RT, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (3×25 mL) and brine 1×25 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 99.6 mg crude material. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow oil (58 mg, 294 μmol, 65.9%).

Workup

temperatureThe reaction mixture was cooled to RT
extractionextracted with ethyl acetate (2×50 mL)
washThe organic phases were washed with water (3×25 mL) and brine 1×25 mL)
dry with materialThe combined organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ca001f3a963a4b8d89a8b8babe5bf691
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772510B2

Reaction notes

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