Dimethylformamide → HCID 86664764, compound

HRID 402416Notes

Reaction equation

HRID 402416 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:22]=[O:23])C.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:13])[C:12]=2[CH:22]=[O:23])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 674955714-(4-Fluoro-phenyl)-1-methyl-1H-[1,2,3]triazoleHCID 178418339Butyllithium

Product 1

HCID 86664764HCID 86664764, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole (709 mg, 4.0 mmol) in THF (20 mL) was added n-BuLi (1.6 M in hexane, 3.0 mL, 4.8 mmol) dropwise at −75° C. under Argon. The resulting solution was stirred at −75° C. for 1 h, then DMF (401 μL, 5.2 mmol) was added dropwise at −75° C. and the reaction mixture was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (773 mg, 94%) as a white solid. MS: m/e=206.2 [M]+.

Workup

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-86ddc39d1344459da33e13ef16ce03b4
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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