Sodium Carbonate → 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol

HRID 58630ノート

反応式

HRID 58630 の反応式
[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[CH2:11]([Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH3:12].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([C:15]([CH2:16][CH2:17][OH:18])=[C:14]([Si:13]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:11][CH3:12])[NH:7]2)=[CH:4][C:3]=1[CH3:10]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 584754055-Chloro-2-iodo-4-methylaniline

生成物 1

HCID 668320342-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol収率 79.2%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

5-chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100° C. for 15 hours. The mixture was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of the title compound as a brown oil.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted in ethyl acetate
  3. washThe organic layer was successively washed with brine, sodium thiosulphate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-cf662b2f82ea4046ac3dbaf33facd596
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

反応ノート

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