Water → HCID 21110080, compound

HRID 1766168Notes

Reaction equation

HRID 1766168 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:20]1.O>CS(C)=O>[CH3:12][C:4]1[CH:3]=[C:2]([N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:20]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 779734-Chloro-2-methylquinolineHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 21110080HCID 21110080, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

5.5 g (31 mmol) of 4-chloro-2-methylquinoline and 8.9 g (65 mmol) of potassium carbonate were added to 4.6 g (26 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 93 cm3 of dimethyl sulfoxide under argon. The reaction mixture was heated at a temperature in the region of 120° C. for 16 h, then it was cooled to a temperature in the region of 20° C. and treated with 250 cm3 of water. The aqueous phase was extracted with 250 cm3 and then 125 cm3 of ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered and then 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 dichloromethane. The fractions comprising the expected product were combined and then concentrated to dryness under reduced pressure (2.7 kPa). 1.4 g of methyl 1-(2-methylquinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were thus obtained in the form of an orange crystalline solid melting at 179° C.

Workup

  1. temperatureit was cooled to a temperature in the region of 20° C.
  2. extractionThe aqueous phase was extracted with 250 cm3
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-e57fcf4b4771408091bdcbae5da18755
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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