ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

2-(Tributylstannyl)pyridine → Methyl 1-methyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylate

HRID 1696317
ノート
印刷プレビュー

反応式

HRID 1696317 の反応式
Br[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>O1CCOCC1.O.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>[CH3:9][N:6]1[C:7](=[O:8])[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:3][C:4]([C:10]([O:12][CH3:13])=[O:11])=[CH:5]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 59354302Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

生成物 1

HCID 66846039Methyl 1-methyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylate収率 39.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (57 mg, 0.23 mmol), 2-(tributylstannyl)pyridine (85 mg, 0.23 mmol) and tetrakis(triphenylphosphine)palladium (13 mg, 0.012 mmol, Strem) were stirred in 1.5 mL of dioxane at 90° C. for 16 h. The reaction mixture was cooled to RT, diluted with H2O and extracted with EtOAc (2×). The combined organic extracts were washed 1× with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude residue by column chromatography (4 g pre-packed column, elution 0-30% EtOAc/Hexanes) gave the title compound (22 mg, 39%) as a light yellow solid. MS m/z: 245 (M+1).

後処理

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed 1× with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue
  7. washby column chromatography (4 g pre-packed column, elution 0-30% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-7e2920749579407ebe360576873552db
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163766B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート