Cesium carbonate → (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one

HRID 70658ノート

反応式

HRID 70658 の反応式
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:33]1[CH:34]=[CH:35][C:36](/[C:41](/[C:49]2[CH:54]=[CH:53][C:52]([C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:51][CH:50]=2)=[CH:42]/[C@@H:43]2[NH:47][C:46](=[O:48])[CH2:45][CH2:44]2)=[N:37][C:38]=1[O:39][CH3:40]>O1CCOCC1.C(OCC)(=O)C.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:55]([C:52]1[CH:53]=[CH:54][C:49](/[C:41](/[C:36]2[CH:35]=[CH:34][C:33]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:38]([O:39][CH3:40])[N:37]=2)=[CH:42]\[C@@H:43]2[NH:47][C:46](=[O:48])[CH2:45][CH2:44]2)=[CH:50][CH:51]=1)([CH3:58])([CH3:57])[CH3:56]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 521585Tris(furan-2-yl)phosphaneHCID 58452636(5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

生成物 1

HCID 67397019(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

Phenylboronic acid (57 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), tri(2-furyl)phosphine (32 mg) and cesium carbonate (151 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42 (80 mg) in 1,4-dioxane (1.5 mL)-water (0.5 mL), and the mixture was stirred at an external temperature of 65° C. for three hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate 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→3:2) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one as an orange oil (81 mg).

後処理

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

出典と根拠

ORDレコード
ord-e796418d2b9f433caca48e576b24ad79
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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