Sodium hydride → HCID 15462806, compound

HRID 1421256Notes

Reaction equation

HRID 1421256 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:25](Cl)[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1>CN(P(N(C)C)(N(C)C)=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:25][C:26]3[CH:34]=[CH:33][C:32]4[O:31][CH2:30][O:29][C:28]=4[CH:27]=3)[C:10]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 15462808HCID 15462808, compound

Product 1

HCID 15462806HCID 15462806, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

To a solution of ethyl 3-(4-methoxyphenyl)pyrrolo[2,3-b]pyridine-2-carboxylate in HMPA stirred at ice bath temperature under an argon atmosphere is added NaH. A solution of piperonyl chloride in HMPA is added and the ice bath removed. The reaction mixture is stirred at room temperature then partitioned between 3 N HCl and EtOAc. The organic extract is washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent is removed in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. customthe ice bath removed
  2. customthen partitioned between 3 N HCl and EtOAc
  3. extractionThe organic extract
  4. washis washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed in vacuo
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-d89a82ee3cf4466d82b1b8f1328d9ac3
Source dataset
uspto-grants-2000_06
Patent number
US06075037

Reaction notes

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