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

HRID 1054601ノート

反応式

HRID 1054601 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
115 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5efec733de7444849b0e22cabc086b77
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

読み込み中…