Sodium Carbonate → 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 1918624ノート

反応式

HRID 1918624 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[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>[OH:18][CH2:17][CH2:16][C:15]1[C:3]2[C:2](=[CH:9][CH:8]=[C:5]([C:6]#[N:7])[CH:4]=2)[NH:1][C:14]=1[Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:11][CH3:12]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 44163954-Amino-3-iodobenzonitrile

生成物 1

HCID 668321333-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile収率 51.8%

試薬・触媒・溶媒 3

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

実験手順

4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 mL; 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 mL) was stirred at 100° C. for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid.

後処理

  1. filtrationThe solution was filtered through celite
  2. additiondiluted in ethyl acetate
  3. washwashed with brine and sodium thiosulphate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-367f3e4ba19f47aa86669b181ccd8139
出典データセット
uspto-grants-2013_12
特許番号
US08618138B2

反応ノート

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