Dimethylformamide → HCID 86664842、化合物

HRID 2365237ノート

反応式

HRID 2365237 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1.[Li]CCCC.CN([CH:21]=[O:22])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][N:2]1[C:6]([CH:21]=[O:22])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:4]=[N:3]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57746172HCID 57746172、化合物HCID 178418339Butyllithium

生成物 1

HCID 86664842HCID 86664842、化合物収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-75 °C

実験手順

To a solution of 2-(1-methyl-1H-[1,2,3]triazol-4-yl)-pyridine (3.52 g, 22 mmol) in THF (112 mL) was added n-BuLi (1.6 M in hexane, 16.5 mL, 4.96 mmol) dropwise at −75° C. and under Ar. The resulted light brown suspension was stirred at −75° C. for 1 h. Then DMF (2.20 mL, 29 mmol) was added dropwise at −75° C. and the yellow solution 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 (3.75 g, 91%) as a white solid. MS: m/e=188.0 [M]+.

後処理

  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)

出典と根拠

ORDレコード
ord-8f35a20d2cbe46eda1964ec8b8f0f3eb
出典データセット
uspto-grants-2014_04
特許番号
US08697696B2

反応ノート

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