Phosphorus oxychloride → Ethyl 4-chloro-5H-pyrrolo(3,4-b)pyridine-6(7H)-carboxylate

HRID 911829Notes

Reaction equation

HRID 911829 reaction equation
O=P(Cl)(Cl)[Cl:3].[N+:6]1([O-])[CH:11]=[CH:10][CH:9]=[C:8]2[CH2:12][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:7]=12>>[Cl:3][C:9]1[CH:10]=[CH:11][N:6]=[C:7]2[CH2:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][C:8]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66995055ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxide

Product 1

HCID 66995010Ethyl 4-chloro-5H-pyrrolo(3,4-b)pyridine-6(7H)-carboxylateYield 46%

Conditions

Temperature
50 °C

Procedure

POCl3 (20 mL, 218 mmol) was added into ethyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate N-oxide (1 g, 4.80 mmol) and heated to 35° C. for 12 hours and 50° C. for another 5 hours. The solvent was evaporated and poured into water. The material was extracted with CH2Cl2, washed with NaHCO3 and brine, dried with Na2SO4, filtered and concentrated. The residue was purified on silica gel to afford the title compound (0.5 g, 45.9% yield).

Workup

  1. customThe solvent was evaporated
  2. additionpoured into water
  3. extractionThe material was extracted with CH2Cl2
  4. washwashed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a4ac172361bf445aadeca13e5805bb13
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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