Phosphorus oxide (P4O10) → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(5-methoxy-2-oxazolyl)-

HRID 1360183Notes

Reaction equation

HRID 1360183 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=O)=[CH:6][N:5]=[C:4]2[NH:16][CH:17]=[CH:18][C:3]=12.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[O:13][C:12]([O:14][CH3:15])=[CH:11][N:10]=2)=[CH:6][N:5]=[C:4]2[NH:16][CH:17]=[CH:18][C:3]=12

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 57928282Glycine, N-[(4-chloro-1H-pyrrolo[2,3-B]pyridin-5-YL)carbonyl]-, methyl ester

Product 1

HCID 579281581H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(5-methoxy-2-oxazolyl)-Yield 28.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl N-[(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)carbonyl]glycinate (167 mg) in chloroform (5 ml) was added diphosphorus pentoxide (886 mg) under ambient temperature, and the mixture was refluxed for 18 hours. The reaction solution was cooled and added to saturated aqueous sodium hydrogencarbonate. The reaction solution was extracted with ethyl acetate. The organic layer was washed with water. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by thin-layer silica gel column chromatography (chloroform:methanol=15:1) to obtain 4-chloro-5-(5-methoxy-1,3-oxazol-2-yl)-1H-pyrrolo[2,3-b]pyridine (45 mg) as a yellowish white solid.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe reaction solution was cooled
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by thin-layer silica gel column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-9ed005870c4b4cc9913efa7d84fad319
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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