1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

HRID 1506192Notes

Reaction equation

HRID 1506192 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1>C(OCC)(=O)C>[NH:12]1[C:16]2=[N+:17]([O-:9])[CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 178526243HCID 178526243, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (25 wt % water content, 12.7 g, 55.2 mmol) in ethyl acetate (30 mL) was gradually added dropwise to 1H-pyrrolo[2,3-b]pyridine (5.14 g, 43.5 mmol) in ethyl acetate (45 mL) cooled to 0° C., and the reaction mixture was stirred at room temperature for one day and then stirred with m-chloroperbenzoic acid (25 wt % water content, 3.93 g, 17.1 mmol) in ethyl acetate (4 mL) at room temperature for 4 hours. The reaction mixture was cooled with ice and filtered, and the resulting solid was purified by silica gel column chromatography (silica gel NH type manufactured by Fuji Silysia Chemical Ltd.: chloroform/methanol=10/1 (v/v)) to give the title compound as a yellow solid (4.95 g, yield 85%).

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. filtrationfiltered
  3. customthe resulting solid was purified by silica gel column chromatography (silica gel NH type manufactured by Fuji Silysia Chemical Ltd.: chloroform/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-91710362fa334398a72066f01755ded9
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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