Water → methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate

HRID 338319

반응식

HRID 338319 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.Br[C:24]1[CH:25]=[C:26]([O:32][CH3:33])[C:27]([O:30][CH3:31])=[CH:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate

생성물 1

HCID 86698666methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate수율 84%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A mixture of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.31 mmol), 4-bromoveratrole (83 mg, 0.37 mmol), and aqueous potassium carbonate solution (2M, 0.62 mL, 1.24 mmol) in toluene (1.8 mL) and ethanol (0.6 mL) was degassed with nitrogen for 5 minutes then treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (13.8 mg, 0.016 mmol). The reaction mixture was heated to 110° C. for 2.5 h. The reaction was cooled to room temperature and poured into water and ethyl acetate. The layers were separated and the aqueous layer was back-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash column chromatography was performed on the crude product using heptanes/ethyl acetate (4:1 to 1:1) to give the title compound (90 mg 84%). MS (ES+) 346.2 (M+H)+. 1H NMR (500 MHz, DMSO-d6) δ 12.05 (br. s., 1H), 8.17 (s, 1H), 7.94 (s, 1H), 7.64 (s, 1H), 7.04 (d, J=8.29 Hz, 1H), 6.98 (s, 1H), 6.93 (d, J=8.29 Hz, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.78 (s, 3H).

후처리

  1. customwas degassed with nitrogen for 5 minutes
  2. temperatureThe reaction was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was back-extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-59c733421cf0401dbf742aa38d4f6cb5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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