Potassium Carbonate → methyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate

HRID 1054601노트

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HRID 1054601 반응식
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15]3)=[CH:10][CH:9]=2)OC1.Br[C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[Cl:34])[NH:30][CH:29]=[C:28]2[CH:35]=[O:36].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.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]>[Cl:34][C:33]1[CH:32]=[C:31]2[C:27]([C:28]([CH:35]=[O:36])=[CH:29][NH:30]2)=[CH:26][C:25]=1[C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15]2)=[CH:12][CH:13]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698604Methyl 3-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)pyrrolidine-1-carboxylate

생성물 1

HCID 86698603methyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate수율 68%

시약·촉매·용매 3

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

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온도
115 °C

실험 절차

To a degassed mixture of methyl 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyrrolidine-1-carboxylate (0.158 g, 0.5 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (142.5 mg, 0.55 mmol) and 2 N aqueous potassium carbonate (1.0 mL, 2.0 mmol) in toluene (3 mL) and EtOH (1 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (36.6 mg, 0.05 mmol). The resulting mixture was heated to 115° C. in a microwave for 30 min. The reaction mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (0:100 to 57:43) to give methyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate (0.13 g, 68%) as a yellow solid, which was used in the next step without further purification.

후처리

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (0:100 to 57:43)

출처 및 근거

ORD 기록
ord-5efec733de7444849b0e22cabc086b77
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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