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

HRID 1878634노트

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HRID 1878634 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
220 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1db14dfe5fcf4e5595c7e889eae89bac
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314120B2

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