Oxygen → 4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445929Notes

Reaction equation

HRID 1445929 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([O-])(C)C.[K+].O=O>C1COCC1.CS(C)=O>[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

6

Reactant 3

HCID 977OxygenHCID 23665647Potassium tert-butoxideHCID 59170308HCID 59170308, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine 2 (0.887 mg, 3.52 mmol) in THF (10 mL), DMSO (2.5 mL), followed by KOtBu (25 mL, 1.0 M in THF) was added dropwise, and then the reaction mixture was treated with O2 for 15 min at room temperature, quenched with saturated NH4Cl (20 mL), extracted with EtOAc (3×60 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4 and evaporated. Flash chromatography of the residue over silica gel, using 20% EtOAc in hexanes to 40% EtOAc in hexanes) gave product 3 as a yellow solid. Yield: 560 mg (98%).

Workup

  1. additionwas added dropwise
  2. customquenched with saturated NH4Cl (20 mL)
  3. extractionextracted with EtOAc (3×60 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-2a17d97acb5540c4b4304b167d41518b
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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