Methyl iodide → HCID 21743857, compound

HRID 1756066Notes

Reaction equation

HRID 1756066 reaction equation
[CH3:1][C:2]1[N:19]=[C:5]2[N:6]([CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:20].[H-].[Na+].[CH3:23]I>C1COCC1>[CH3:1][C:2]1[N:19]=[C:5]2[N:6]([CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:12][CH3:23])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19916800HCID 19916800, compound

Product 1

HCID 21743857HCID 21743857, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-dimethyl-7-(2-phenyl-2-hydroxyethyl)pyrrolo[2,3-b]pyridine (as the base) (266 mg, 1.0 mmol) in 25 ml dry THF was deaerated and treated with 55% NaH dispersion in oil (48 mg, 1.1 mmol) for 30 min. Methyl iodide (62 μl, 1.0 mmol) was added and allowed to react for 50 min. The solvent was evaporated and the residue partitioned between 100 ml CH2Cl2 and 20 ml 5% NaOH. The organic layer was dried over MgSO4 and evaporated. The residue was chromatographed (silica, CH2Cl2 saturated with NH3). Pure fractions were pooled and evaporated leaving a gum which partly crystallized. Trituation with diethyl ether furnished 207 mg (65%) pure title compound.

Workup

  1. customto react for 50 min
  2. customThe solvent was evaporated
  3. customthe residue partitioned between 100 ml CH2Cl2 and 20 ml 5% NaOH
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed (silica, CH2Cl2 saturated with NH3)
  7. customevaporated
  8. customleaving a gum which
  9. custompartly crystallized

Sources & evidence

ORD record
ord-9d8ada02b3c342c780e755e616336e9f
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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