Sodium hydride → 3-Iodo-4-methoxy-1-[1-(methoxymethyl)propyl]-1H-pyrrolo[3,2-c]pyridine

HRID 2206005Notes

Reaction equation

HRID 2206005 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[CH:26]([CH2:30][CH3:31])[CH2:27][O:28][CH3:29])(=O)=O)=CC=1>CN(C=O)C>[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:26]([CH2:30][CH3:31])[CH2:27][O:28][CH3:29])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127007761-Methoxybutan-2-yl 4-methylbenzene-1-sulfonateHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 1179879873-Iodo-4-methoxy-1-[1-(methoxymethyl)propyl]-1H-pyrrolo[3,2-c]pyridineYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (0.500 g) in DMF (15 mL) was added sodium hydride (60% dispersion in mineral oil, 18.3 mg), and the mixture was stirred at room temperature for 1 hr, 1-methoxybutan-2-yl 4-methylbenzenesulfonate (1.18 g) 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 (589 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-216bb876818b457b863954b173b2ee8e
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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