Potassium tert-butoxide → 4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445941Notes

Reaction equation

HRID 1445941 reaction equation
C([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH:10]=[C:9]1[CH3:19])C1C=CC=CC=1.CC(C)([O-])C.[K+]>C1COCC1>[CH3:18][O:17][C:12]1[C:11]2[CH:10]=[C:9]([CH3:19])[NH:8][C:16]=2[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59170308HCID 59170308, compound

Product 1

HCID 534128814-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine (2) (0.887 g, 3.51 mmole) in anhydrous THF (10 mL) dimethyl sulfoxide (25 mL) was added slowly (via a syringe) and the mixture was cooled to 0° C. Potassium tert-butoxide (1M in THF, 25 mL, 25 mmole) was added slowly. Oxygen was bubbled through the mixture for 45 minutes. The reaction was quenched with saturated ammonium chloride solution, the mixture was extracted with ethyl acetate (3×50 mL). The organic layer was separated, dried over magnesium sulphate and concentrated. The residue was purified by column chromatography (3:1 Hex:EtOAc) to afford intermediate (3). Yield: 1.06 g >100%

Workup

  1. customOxygen was bubbled through the mixture for 45 minutes
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (3:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-5786cab8981c45ff8b531f00a4aa56a0
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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