Toluene → 5-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carbaldehyde

HRID 1054591

반응식

HRID 1054591 반응식
[N:1]1([C:5](=[O:21])[CH2:6][C:7]2[CH:12]=[CH:11][C:10](B3OCC(C)(C)CO3)=[CH:9][CH:8]=2)[CH2:4][CH2:3][CH2:2]1.Br[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][C:31]=1[Cl:32])[NH:28][CH:27]=[C:26]2[CH:33]=[O:34].C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>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].CCO>[N:1]1([C:5](=[O:21])[CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][C:31]=3[Cl:32])[NH:28][CH:27]=[C:26]4[CH:33]=[O:34])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4]1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 866985921-(Azetidin-1-yl)-2-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethanone

생성물 1

HCID 866985935-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carbaldehyde수율 42%

시약·촉매·용매 2

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

반응 조건

온도
120 °C

실험 절차

To a degassed mixture of 1-(azetidin-1-yl)-2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethanone (0.78 g, 2.7 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (700 mg, 2.7 mmol) and 2 M aqueous K2CO3 (5.4 mL, 10.8 mmol) in a solvent mixture of toluene and EtOH (v/v=3/1, 14 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (197.6 mg, 0.27 mmol). The reaction mixture was stirred under microwave irradiation at 120° C. for 30 min. After cooling to room temperature, the reaction mixture was partitioned between water and EtOAc (50 mL/50 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (first EtOAc in Petroleum 25%, then MeOH in DCM 10%) to give 5-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carbaldehyde (0.4 g, 42%) as a brown solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water and EtOAc (50 mL/50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column (first EtOAc in Petroleum 25%

출처 및 근거

ORD 기록
ord-5f8344630ee04ec7a6af1f8fb9d37e88
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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