Methyl formate → 7H-Pyrrolo[3,4-b]pyridin-7-one, 5,6-dihydro-5-hydroxy-6-phenyl-

HRID 1493136Notes

Reaction equation

HRID 1493136 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:21](OC)=[O:22]>O1CCCC1.CCCCCC>[OH:22][CH:21]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7865Methyl formateHCID 7020657N-PhenylpicolinamideHCID 178418339Butyllithium

Product 1

HCID 100139217H-Pyrrolo[3,4-b]pyridin-7-one, 5,6-dihydro-5-hydroxy-6-phenyl-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of N-phenyl-2-pyridinecarboxamide (1.00 g) in dry tetrahydrofuran (20 mL) under N2 atmosphere at -78° C., was added n-butyllithium in hexane (4.0 mL, 2.5M). This mixture was allowed to stir for one hour. Methyl formate (0.62 mL) in dry tetrahydrofuran (5 mL) was added rapidly dropwise. After addition, the cold bath was removed and the mixture warmed to room temperature over two hours. The reaction was quenched with water and the tetrahydrofuran was evaporated in vacuo. The residue was extracted with ethyl acetate and dried (K2CO3). Purification was effected by flash chromatography on silica gel using ethyl acetate/hexane (6/4) as eluant (Rf =0.1). The yield was 310 mg (27.4%).

Workup

  1. additionAfter addition
  2. customthe cold bath was removed
  3. customThe reaction was quenched with water
  4. customthe tetrahydrofuran was evaporated in vacuo
  5. extractionThe residue was extracted with ethyl acetate
  6. dry with materialdried (K2CO3)
  7. customPurification

Sources & evidence

ORD record
ord-5db1d4728beb4930af20d77a08ed0800
Source dataset
uspto-grants-1991_06
Patent number
US05021418

Reaction notes

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