Sodium hydride → 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

HRID 2206087Notes

Reaction equation

HRID 2206087 reaction equation
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:26][CH:27]2[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]2)(=O)=O)=CC=1>CN(C=O)C>[CH3:32][C:29]1([CH3:33])[O:28][CH:27]([CH2:26][N:4]2[C:5]3[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH3:12])[C:6]=3[C:2]([I:1])=[CH:3]2)[CH2:31][O:30]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 1179877651-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine in DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 73.0 mg), and the mixture was stirred at room temperature for 1 hr, (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (523 mg) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (122 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ba43fa91177a49b698fafc989c7b2cc1
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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