Cesium carbonate → HCID 67400008、化合物

HRID 70700ノート

反応式

HRID 70700 の反応式
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]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 634876Binap, (A+-)-HCID 58452310HCID 58452310、化合物

生成物 1

HCID 67400008HCID 67400008、化合物収率 75%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b51199273cbc416eb7e2ad12e5be6267
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

読み込み中…