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

HRID 1054591

反応式

HRID 1054591 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-5f8344630ee04ec7a6af1f8fb9d37e88
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

関連ノート

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