Benzyl 2-(tributylstannyl)acrylate → Benzyl 2-(3-methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)acrylate

HRID 887148ノート

反応式

HRID 887148 の反応式
Br[C:2]1[C:3]2[N:4]([C:8]([CH3:11])=[N:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:17](=[CH2:28])[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])CCC>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Cl>[CH3:11][C:8]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:17](=[CH2:28])[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[C:3]2=[N:10][N:9]=1

参加物

6

反応物 2

HCID 66838741Benzyl 2-(tributylstannyl)acrylate2 回HCID 669245028-Bromo-3-methyl-[1,2,4]triazolo[4,3-A]pyridine

生成物 1

HCID 66924470Benzyl 2-(3-methyl[1,2,4]triazolo[4,3-a]pyridin-8-yl)acrylate収率 73%

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 0.13 g (0.61 mmol) of 8-bromo-3-methyl[1,2,4]triazolo[4,3-a]pyridine from Step B above in 4 mL of anhydrous THF was added a solution of 0.36 g (0.80 mmol) of benzyl 2-(tributylstannyl)acrylate (see Intermediate 62, Step B) in 1 mL of anhydrous THF, 0.11 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.067 g (0.67 mmol) of copper (I) chloride. The reaction mixture was heated to 60° C. for 6 h, cooled and filtered through a pad of Celite®. The pad was washed with 15 mL of a dichloromethane and the combined filtrates were evaporated to dryness. The crude residue was purified by silica gel chromatography eluting with a 0-6% methanol in ethyl acetate gradient to afford the title compound (0.13 g, 73%). LC-MS: m/z (ES) 294 (MH)+.

後処理

  1. temperaturecooled
  2. filtrationfiltered through a pad of Celite®
  3. washThe pad was washed with 15 mL of a dichloromethane
  4. customthe combined filtrates were evaporated to dryness
  5. customThe crude residue was purified by silica gel chromatography
  6. washeluting with a 0-6% methanol in ethyl acetate gradient

出典と根拠

ORDレコード
ord-1b45fe5e038a4dd0917d21bd16cba2c8
出典データセット
uspto-grants-2012_08
特許番号
US08247415B2

反応ノート

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