Cesium carbonate → HCID 67400008, 화합물

HRID 70700노트

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HRID 70700 반응식
Br/[CH:2]=[C:3](/[C:14]1[N:19]=[C:18]([O:20][CH3:21])[C:17]([Cl:22])=[CH:16][CH:15]=1)\[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:10]([C:7]1[CH:8]=[CH:9][C:4](/[C:3](/[C:14]2[CH:15]=[CH:16][C:17]([Cl:22])=[C:18]([O:20][CH3:21])[N:19]=2)=[CH:2]\[N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:5][CH:6]=1)([CH3:13])([CH3:12])[CH3:11]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 634876Binap, (A+-)-HCID 58452310HCID 58452310, 화합물

생성물 1

HCID 67400008HCID 67400008, 화합물수율 75%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

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온도
130 °C

실험 절차

A solution of 6-[(E)-2-bromo-1-(4-tert-butylphenyl)ethenyl]-3-chloro-2-methoxypyridine obtained in Reference Example 4-7 (109 mg), 2-pyrrolidone (73 mg), tris(dibenzylideneacetone)dipalladium(0) (11 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg) and cesium carbonate (329 mg) in toluene (3 mL) was stirred at an external temperature of 130° C. for four hours in a nitrogen atmosphere. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to give 1-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a yellow powder (82 mg, 75%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

출처 및 근거

ORD 기록
ord-b51199273cbc416eb7e2ad12e5be6267
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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