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

HRID 1714071노트

반응식

HRID 1714071 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-845bee40f05f47debaa01d4b461b3d88
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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