Sodium Carbonate → methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

HRID 1714071ノート

反応式

HRID 1714071 の反応式
Br[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.C([O-])([O-])=O.[Na+].[Na+].[CH:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O)=[O:34]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:2]=2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH:33]=[O:34])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 68501826methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

生成物 1

HCID 86604971methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate収率 40%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in dioxane (0.15 M) were added Na2CO3 (6 eq, 2 M aqueous solution), 1.6 eq of (2-formylphenyl)boronic acid and 0.2 eq of bis(triphenylphosphine)-palladium(II) dichloride. The mixture was heated at reflux for 1 h. The reaction mixture was filtered and the filtrate diluted with EtOAc. The organic phase was washed with brine and dried (Na2SO4) before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (Biotage cartridge Si25M, 1:9 EtOAc/PE) to afford the title compound (40%); MS (ES+) m/z 448 (M+H)+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate diluted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationbefore being filtered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified by flash chromatography (Biotage cartridge Si25M, 1:9 EtOAc/PE)

出典と根拠

ORDレコード
ord-845bee40f05f47debaa01d4b461b3d88
出典データセット
uspto-grants-2010_09
特許番号
US07795247B2

反応ノート

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