Sodium Carbonate → HCID 86761176, 화합물

HRID 1714066

반응식

HRID 1714066 반응식
Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[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:35]([C:37]1[CH:41]=[CH:40][O:39][C:38]=1B(O)O)=[O:36].B(O)O>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>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:38]1[O:39][CH:40]=[CH:41][C:37]=1[CH:35]=[O:36])([CH3:28])([CH3:27])[CH3:26]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 61668Boronic Acid2회HCID 37393373-Formylfuran-2-boronic acidHCID 29943315HCID 29943315, 화합물

생성물 1

HCID 86761176HCID 86761176, 화합물수율 38%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in Example 1, Step 1) in dioxane (0.04 M) was added Na2CO3 (5 eq, 2 M aqueous solution), 3-formylfuran-2-boronic acid (1.4 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.2 eq). The mixture was heated at reflux for 20 mins, at which point the heat was removed and the reaction cooled slightly to allow addition of a further 1 eq of boronic acid. The reaction was then heated for a further 1 h at reflux. Again, the reaction was cooled slightly to allow addition of a further 0.5 eq of boronic acid. After heating for a further 30 mins, the reaction was allowed to cool to RT, filtered and the filtrate diluted with EtOAc. The organic phase was washed with H2O and dried (Na2SO4) before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (10-20% EtOAc/PE) to afford the title compound as an oil (38%); MS (ES+) m/z 466 (M+H)+, 488 (M+Na)+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 mins, at which
  3. customwas removed
  4. temperaturethe reaction cooled slightly
  5. temperatureThe reaction was then heated for a further 1 h
  6. temperatureat reflux
  7. temperatureAgain, the reaction was cooled slightly
  8. temperatureAfter heating for a further 30 mins
  9. filtrationfiltered
  10. additionthe filtrate diluted with EtOAc
  11. washThe organic phase was washed with H2O
  12. dry with materialdried (Na2SO4)
  13. filtrationbefore being filtered
  14. concentrationconcentrated in vacuo
  15. customThe crude was purified by flash chromatography (10-20% EtOAc/PE)

출처 및 근거

ORD 기록
ord-56213daeba644e7695ed53485c57370d
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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