Potassium Carbonate → HCID 178526258, compound

HRID 1878611Notes

Reaction equation

HRID 1878611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.C1C=C(Cl)C=C(C(OO)=[O:19])C=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:19])=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526258HCID 178526258, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (see Journal of Organic Chemistry (2006), 71 (10), 4021-4023) (1 eq, 18.6 g, 122 mmol) in CHCl3 at 0° C., mCPBA (1 eq, 122 mmol, 27.3 g) is added portionwise over 20 min by keeping the temperature at 0-10° C. The resulting suspension is stirred for 30 min at 0-5° C., warmed up to r.t. and stirred for another 1 h. The reaction mixture is diluted with water (300 ml), then K2CO3 (22 g) is added, and the mixture is stirred for 30 min. The layers are separated and the aqueous layer is extracted with DCM/Isopropanol (3:1). The combined organic layers are washed with aqueous K2CO3 solution, dried over MgSO4, filtered, and concentrated to give the title compound; [M+H]+=169.

Workup

  1. customat 0-10° C
  2. temperaturewarmed up to r.t.
  3. stirringstirred for another 1 h
  4. stirringthe mixture is stirred for 30 min
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with DCM/Isopropanol (3:1)
  7. washThe combined organic layers are washed with aqueous K2CO3 solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5a73401cb9d34cb1bbdd3cbd9f0ae10e
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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