Potassium Carbonate → 6-Chloro-5-phenyl-1H-indole-3-carbaldehyde

HRID 338221

反応式

HRID 338221 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH:12]=[O:13].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.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:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH:12]=[O:13])=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehyde

生成物 1

HCID 866985726-Chloro-5-phenyl-1H-indole-3-carbaldehyde収率 98%

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

実験手順

A mixture of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (200 mg, 0.77 mmol), phenyl boronic acid (114 mg, 0.93 mmol), 2N aqueous potassium carbonate (1.15 mL, 3.10 mmol) in toluene (3.3 mL) and EtOH (1.1 mL) was degassed with N2, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (56.6 mg, 0.077 mmol), and degassed again with N2. The mixture was subjected to microwave irradiation conditions at 120° C. for 30 minutes. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (0-46% EtOAc/petroleum ether) to afford the title compound (190 mg, 98% yield) as a yellow solid.

後処理

  1. customwas degassed with N2
  2. customdegassed again with N2
  3. customirradiation conditions at 120° C. for 30 minutes
  4. additiondiluted with water
  5. extractionextracted with EtOAc (50 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography (0-46% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-bc14fd9a3671457d8e8bfb84eb9723b6
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

関連ノート

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