Phosphorus oxychloride → ethyl-7-chloro-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate

HRID 2410935Notes

Reaction equation

HRID 2410935 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[NH:10][C:3]=12.O=P(Cl)(Cl)[Cl:19]>C(#N)C>[CH2:15]([O:14][C:12]([C:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([Cl:19])=[C:3]2[NH:10][C:9]=1[CH3:11])=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469265HCID 178469265, compound

Product 1

HCID 67774803ethyl-7-chloro-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 7-hydroxy-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylate (44.0 g, 0.20 mol) is suspended in dry acetonitrile (400 mL). After addition of POCl3 (47 mL, 0.50 mol) the stirred reaction mixture is heated to reflux for 4 hours. The volatiles are removed under reduced pressure. The residue is suspended in ice-cold water (500 mL) and carefully neutralized to pH 8 by dropwise addition of 6N NaOH. Stirring is continued at ambient temperature over night. The pH is readjusted to 8, the product is filtered, washed with several small portions of water and dried in vacuum at 50° C. for 24 hours to yield the title compound as off-white solid.

Workup

  1. customthe stirred reaction mixture
  2. temperatureis heated
  3. temperatureto reflux for 4 hours
  4. customThe volatiles are removed under reduced pressure
  5. additioncarefully neutralized to pH 8 by dropwise addition of 6N NaOH
  6. waitis continued at ambient temperature over night
  7. filtrationthe product is filtered
  8. washwashed with several small portions of water
  9. customdried in vacuum at 50° C. for 24 hours

Sources & evidence

ORD record
ord-166ec474213f4b688f1929c4f34a363c
Source dataset
uspto-grants-2014_08
Patent number
US08816085B2

Reaction notes

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