Diethyl Ether → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 2401536Notes

Reaction equation

HRID 2401536 reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:13])=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>O.CCCCCC>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridine 7-oxide (1.35 g, 10 mmol) and phosphorous oxychloride (7.6 ml) was refluxed for 6 hours. After cooling down the reaction mixture to room temperature, ice (90 ml) was added and the mixture was basified to pH 9 with a saturated aqueous solution of potassium carbonate. The brownish solid was filtered, washed with water, hexane and diethyl ether (547 mg, 3.6 mmol, 36%). LC/MS (LCT) Rt 5.74 [M+H]+ 153, 155.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe brownish solid was filtered

Sources & evidence

ORD record
ord-a52bebcd73124e3abd4e70d0dbd02188
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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