3-Bromoaniline → 3-(1H-indol-6-yl)-phenylamine

HRID 240181

反応式

HRID 240181 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](B(O)O)[CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH2:17])[CH:18]=[CH:19][CH:20]=3)[CH:8]=2)[CH:3]=[CH:2]1

参加物

7

反応物 4

HCID 115623-BromoanilineHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27632051H-Indol-6-ylboronic acid

生成物 1

HCID 668660463-(1H-indol-6-yl)-phenylamine収率 79%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

Indole-6-boronic acid (0.140 g, 0.872 mmol) and 3-bromoaniline (0.063 mL, 0.581 mmol) were combined in dioxane (2 mL) in a flame-dried, round-bottom flask. K3PO4 (1.27M, 0.778 mL, 0.99 mmol), PCy3 (0.004 g, 0.014 mmol), and Pd2(dba)3 (0.005 g, 0.006 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.096 g in 79% yield.

後処理

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.096 g in 79% yield

出典と根拠

ORDレコード
ord-d3a431b35c7c43d3b10024fa6e4da94d
出典データセット
uspto-grants-2014_02
特許番号
US08642788B2

関連ノート

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