Ethyl 3-(trimethylsilyl)propynoate → 1-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

HRID 1454976ノート

反応式

HRID 1454976 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.[CH3:17][Si:18]([CH3:27])([CH3:26])[C:19]#[C:20][C:21](OCC)=[O:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])[C:21](=[O:22])[C:20]#[C:19][Si:18]([CH3:27])([CH3:26])[CH3:17])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 568601Ethyl 3-(trimethylsilyl)propynoateHCID 575312355-Bromo-2-(2,6-difluorobenzyl)pyridine

生成物 1

HCID 575312421-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 5-bromo-2-(2,6-difluorobenzyl)pyridine (5.6 g) in THF was added ethyl 3-(trimethylsily)propynoate (4.2 mL) and LHMD (42 mL, 1N in THF) at −78° C. The mixture was warmed to 0° C. and stirred in additional 2 h. The reaction was complete by TLC and quenched with NH4Cl, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4 and condensed in vacuo. The crude compound was purified by silica gel (hexanes/methylene chloride) to give the desired product.

後処理

  1. customquenched with NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4 and condensed in vacuo
  5. customThe crude compound was purified by silica gel (hexanes/methylene chloride)

出典と根拠

ORDレコード
ord-bae2a9105a944a8293550526683bebbf
出典データセット
uspto-grants-2009_01
特許番号
US07482345B2

反応ノート

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