Sodium Carbonate → 2-(Triethylsilyl)-1H-pyrrolo[2,3-b]pyridine-3-ethanol

HRID 1948622ノート

反応式

HRID 1948622 の反応式
I[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([Si:11]([CH2:19][CH3:20])([CH2:17][CH3:18])[C:12]#[C:13][CH2:14][CH2:15][OH:16])[CH3:10].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.CCOC(C)=O.CCOCC>[CH2:19]([Si:11]([CH2:9][CH3:10])([CH2:17][CH3:18])[C:12]1[NH:8][C:3]2=[N:4][CH:5]=[CH:6][CH:7]=[C:2]2[C:13]=1[CH2:14][CH2:15][OH:16])[CH3:20]

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 27631512-Amino-3-iodopyridine

生成物 1

HCID 153510022-(Triethylsilyl)-1H-pyrrolo[2,3-b]pyridine-3-ethanol収率 80%

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 21584169Diethylether ethylacetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-iodopyridin-2-amine (0.46 g, 2.09 mmole), 4-(triethylsilyl)but-3-in-1-ol (0.58 g, 3.14 mmole), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (0.083 g, 0.105 mmole), lithium chloride (0.086 g, 2.09 mmole) and sodium carbonate (0.44 g, 4.18 mmole) in DMF (21 ml) was stirred under nitrogen for 15 hours at 100° C. The reaction mixture was cooled to RT, EtOAc/ether (1:1) was added and the mixture was poured into H2O. The two-phase suspension was filtered through filter earth. After separating the phases the aqueous phase was extracted with EtOAc (2×). The organic phases were combined and washed with H2O and with saturated NaCl solution and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator. Column chromatography of the residue (n-hexane/EtOAc=2:1, then n-hexane/EtOAc=1:1) yielded 2-(2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (0.46 g, 80%).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationThe two-phase suspension was filtered
  3. filtrationthrough filter earth
  4. customAfter separating the phases the aqueous phase
  5. extractionwas extracted with EtOAc (2×)
  6. washwashed with H2O and with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtering off the drying agent the solvents
  9. customwere removed on a rotary evaporator

出典と根拠

ORDレコード
ord-43627da9ba3f47e29089f3068481d981
出典データセット
uspto-grants-2013_03
特許番号
US08399503B2

反応ノート

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