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

HRID 1948622Notes

Reaction equation

HRID 1948622 reaction equation
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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584169Diethylether ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-43627da9ba3f47e29089f3068481d981
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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