Cesium carbonate → 2-Butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-one

HRID 1878634ノート

反応式

HRID 1878634 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:27])[CH:24]=2)[C:19]1=[O:28])[CH2:15][CH2:16][CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]I.C(OCC)(=O)C.O>[CH2:14]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:27][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][C:7]=3[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:24]=2)[C:19]1=[O:28])[CH2:15][CH2:16][CH3:17]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 27629283-Bromo-4-phenylpyridineHCID 138973842-Butyl-5-hydroxyisoindolin-1-one

生成物 1

HCID 534772442-Butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-one収率 21%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
220 °C

実験手順

A mixture of 3-bromo-4-phenylpyridine (50 mg, 0.213 mmol), 2-butyl-5-hydroxy-isoindolin-1-one (88 mg, 0.427 mmol), Cs2CO3 (139 mg, 0.427 mmol), CuI (16.3 mg, 0.085 mmol) and 2,2,6,6-tetramethyl-3.5-heptanedione (53 μL, 0.256 mmol) in degassed N-methylpyrrolidone (NMP) (2 mL) was stirred and heated in the microwave (220° C., 300 W, 30 min). Two of those reactions were combined, excess water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were extracted with aqueous HCl (2 M) and the combined extracts were basified with aqueous NaOH (2 M) followed by extraction with ethyl acetate. The combined organic layers were washed with water and dried over MgSO4. Purification by HPLC provided 2-butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-one (16 mg, 8%).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with aqueous HCl (2 M)
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. customPurification by HPLC

出典と根拠

ORDレコード
ord-1db14dfe5fcf4e5595c7e889eae89bac
出典データセット
uspto-grants-2012_11
特許番号
US08314120B2

反応ノート

読み込み中…