Potassium Carbonate → 4-(3-Chloro-5-nitropyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridine

HRID 2117184Notes

Reaction equation

HRID 2117184 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=2[CH:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[C:23]([Cl:24])=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1>CC#N>[Cl:24][C:23]1[C:18]([O:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:1][CH:2]=[CH:3][C:4]=23)=[N:19][CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27631062,3-Dichloro-5-nitropyridineHCID 1785164671H-pyrrolo[2,3-b]pyridin-4-ol

Product 1

HCID 210816604-(3-Chloro-5-nitropyridin-2-yloxy)-1H-pyrrolo[2,3-b]pyridineYield 54.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridin-4-ol (210 mg, 1.56 mmol, see: Thibault, C. et al. Org. Lett. 2003, 5, 5023) in 3 mL of MeCN was added K2CO3 (240 mg, 1.74 mmol). The suspension was stirred for 10 min and treated with 2,3-dichloro-5-nitropyridine (270 mg, 1.40 mmol, see: Koch, V. and Schnatterer, S. Synthesis, 1990, 499). The reaction mixture was stirred for 12 h and quenched with 20 mL of H2O. The solution was extracted with EtOAc and the organic layer was washed with brine, and dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash column chromatography (ISCO RediSep® silica gel cartridge) to give the title compound (220 mg, 54%). MS (ESI) m/z 291.1 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 12 h
  2. customquenched with 20 mL of H2O
  3. extractionThe solution was extracted with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration in vacuo
  7. customthe residue was purified by flash column chromatography (ISCO RediSep® silica gel cartridge)

Sources & evidence

ORD record
ord-dbf9094b01a84ad8aaf0b700f064db1d
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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