Potassium Carbonate → HCID 86698613、化合物

HRID 1054609ノート

反応式

HRID 1054609 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)=[CH:10][CH:9]=2)OC1.Br[C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[Cl:37])[NH:33][CH:32]=[C:31]2[CH:38]=[O:39].C(=O)([O-])[O-].[K+].[K+]>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]>[Cl:37][C:36]1[CH:35]=[C:34]2[C:30]([C:31]([CH:38]=[O:39])=[CH:32][NH:33]2)=[CH:29][C:28]=1[C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[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 86698612tert-Butyl 3-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86698613HCID 86698613、化合物収率 39.7%

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
120 °C

実験手順

To a degassed mixture of tert-butyl 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyrrolidine-1-carboxylate (85 mg, 0.237 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (67.3 mg, 0.26 mmol) and 2 N aqueous potassium carbonate (0.47 mL, 0.94 mmol) in toluene (1.12 mL) and ethanol (0.38 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17.3 mg, 0.0237 mmol). The reaction mixture was heated to 120° C. in a microwave for 30 min. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (EtOAc/petroleum ether=1:2) to give tert-butyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate (40 mg) as a yellow solid. MS (ES+) 447.0 (M+Na)+.

後処理

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (EtOAc/petroleum ether=1:2)

出典と根拠

ORDレコード
ord-3a80c556e3324bbda87bfbfe6440e2a4
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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