Cesium carbonate → Methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate

HRID 715968ノート

反応式

HRID 715968 の反応式
Br[C:2]1[C:3]([CH2:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)=[C:4]([C:9]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:2]2[N:22]3[CH2:23][CH2:24][CH2:25][CH:21]3[CH2:20][CH2:19][C:3]=2[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:18]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 70982675Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate2 回

生成物 1

HCID 70983965Methyl 7-(2,2-dimethyl-propionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate収率 50.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)-benzoate (Intermediate 35, 2.05 g), palladium acetate (0.282 g), cesium carbonate (3.26 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (1.557 g) in toluene (40 mL) was stirred and heated at 100° C. under nitrogen for one hour. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give methyl 7-(2,2-dimethylpropionylamino)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-6-carboxylate (0.826 g) as a pale yellow solid.

後処理

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

出典と根拠

ORDレコード
ord-e64dfdef5a6f460385b3dba91bb4f549
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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