Potassium Fluoride → 5-(2-Methyl-pyridin-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 1930836ノート

反応式

HRID 1930836 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].[K+].Cl[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 522689Potassium FluorideHCID 5813924-Chloro-2-methylpyridineHCID 16102684Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)isoindoline-2-carboxylate

生成物 1

HCID 577532995-(2-Methyl-pyridin-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester収率 69%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture containing 1.4 mmol 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester, 4.8 mmol potassium fluoride, 1.4 mmol 4-chloro-2-picoline (commercial) and 0.03 mmol bis(tri-tert.-butylphosphine)palladium in 5 ml degazed dioxane was stirred at 100° C. for 1.5 hours. The solvent was removed in vacuo. The residue was taken in ethyl acetate. The mixture was washed twice with water. The aqueous layer was extracted once with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified on a 20 g Flashpack cartridge (Eluent: Heptane/AcOEt) to afford the title compound as a yellow oil (69% yield). MS (m/e): 311.2 ([M+H]+, 100%)

後処理

  1. customThe solvent was removed in vacuo
  2. washThe mixture was washed twice with water
  3. extractionThe aqueous layer was extracted once with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was purified on a 20 g Flashpack cartridge (Eluent: Heptane/AcOEt)

出典と根拠

ORDレコード
ord-7aa24fe4b5c34424b01488537a0cae15
出典データセット
uspto-grants-2012_05
特許番号
US08188139B2

反応ノート

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