1H-Pyrrolo(2,3-b)pyridine → HCID 21110064, compound

HRID 1766145Notes

Reaction equation

HRID 1766145 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>CN(C)C=O>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydrideHCID 691404-Chloroquinoline

Product 1

HCID 21110064HCID 21110064, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

9 g (76.3 mmol) of 1H-pyrrolo[2,3-b]pyridine were added with stirring to 100 cm3 of dimethylformamide under an argon atmosphere at a temperature in the region of 20° C., and 2.7 g of 75% sodium hydride (84 mmol) were gradually added. After stirring at a temperature in the region of 20° C. for 10 minutes, a solution of 12.5 g (76.4 mmol) of 4-chloroquinoline in 100 cm3 of dimethylformamide was added and then the reaction mixture was heated at a temperature in the region of 100° C. for 15 h. After concentrating to dryness under reduced pressure (2.7 kPa), the residue was taken up in 300 cm3 of water. A first precipitate formed and then a second, which were filtered off. The 2 batches were combined and dissolved in 300 cm3 of dichloromethane. After separating by settling, the organic phase was dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution being carried out with a cyclohexane/ethyl acetate (50/50 by volume) mixture. The fractions comprising the expected product were combined and then concentrated to dryness under reduced pressure (2.7 kPa). 6.6 g of 1-(quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine were thus obtained in the form of a white solid. Mass spectrum: EI: m/z=245 M+; base peak m/z=244 (M−H)+.

Workup

  1. additionwere gradually added
  2. temperaturethe reaction mixture was heated at a temperature in the region of 100° C. for 15 h
  3. concentrationAfter concentrating to dryness under reduced pressure (2.7 kPa)
  4. customA first precipitate formed
  5. filtrationa second, which were filtered off
  6. dissolutiondissolved in 300 cm3 of dichloromethane
  7. customAfter separating
  8. dry with materialthe organic phase was dried over magnesium sulfate
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  10. customThe residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-370993e54bf34d83a429972e73cd19ce
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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