Sodium Chlorite → 1-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

HRID 43265Notes

Reaction equation

HRID 43265 reaction equation
[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]([CH:19]=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:24]Cl=O.[Na+]>CC(O)(C)C.CC(=CC)C.O>[CH2:1]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]([C:19]([OH:24])=[O:20])=[C:9]1[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 23668197Sodium Chlorite2×HCID 446084491-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde2×

Product 1

HCID 446086091-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent2×

Procedure

To a solution of 1-benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (Compound 7, 20 mg, 0.065 mmol) in t-BuOH (1.5 ml) and 2-methyl-2-butene (1 ml) was added a solution of NaH2PO4 (94 mg, 0.78 mmol) and NaClO2 (80%, 73 mg, 0.65 mmol) in H2O (1.5 ml). The mixture was stirred at room temperature and additional 2-methyl-2-butene and a solution of NaH2PO4 and NaClO2 in H2O were added at the above ratio every 6-16 h until the progress of the reaction was satisfactory. The reaction mixture was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes) to yield the title compound.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (×3)
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a10d414e709843d2aa0abca533c82e33
Source dataset
uspto-grants-2013_09
Patent number
US08536339B2

Reaction notes

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