2-Methyl-2-butene → 1-Methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

HRID 82323Notes

Reaction equation

HRID 82323 reaction equation
[CH3:1][N:2]1[C:6]2=[CH:7][N:8]=[CH:9][CH:10]=[C:5]2[C:4]([CH:11]=[O:12])=[CH:3]1.CC(=CC)C.[O-:18]Cl=O.[Na+]>C1COCC1.C(O)(C)(C)C.O>[CH3:1][N:2]1[C:6]2=[CH:7][N:8]=[CH:9][CH:10]=[C:5]2[C:4]([C:11]([OH:18])=[O:12])=[CH:3]1

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 824155781-Methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxaldehyde

Product 1

HCID 682874761-Methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acidYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-methyl-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (WO 05066132) (6.5 g, 40.6 mmol) was dissolved in a mixture solvent of THF (120 mL) and t-butyl alcohol (40 mL) under nitrogen. A 2M 2-methyl-2-butene solution in THF (120 mL, 46 mmol) was added followed by a solution of NaClO2 (11.02 g, 122 mmol) and NaH2PO4 (21.9 g, 183 mmol) in water (30 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. The reaction mixture was concentrated in vacuo to remove organic solvents, and the residue was filtered. The precipitate contained the title compound as white solid in 57% yield, 4.1 g.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove organic solvents
  3. filtrationthe residue was filtered

Sources & evidence

ORD record
ord-2de069f74d6c49228d489223629a5415
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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