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

HRID 82295Notes

Reaction equation

HRID 82295 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 of THF (120 mL) and tert-butyl alcohol (40 mL) under nitrogen. 2-Methyl-2-butene (120 mL of a 2M solution in THF, 46 mmol) was added followed by a solution of NaClO2 (11.0 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 a 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-ec63ee03d324411dbd64d67895ec132c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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