Water → HCID 9817473, compound

HRID 1063247Notes

Reaction equation

HRID 1063247 reaction equation
[C:1]([N:9]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C=O)C>[C:1]([N:9]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH3:24])[C:11]=2[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 363110HCID 363110, compound

Product 1

HCID 9817473HCID 9817473, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-benzoyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (3.0 g, 10.9 mmole) in dry DMF (75 mL) at 5° C. was added 60% NaH (0.52 g, 13.1 mmole). After 10 min, methyliodide (7.80 g, 55 mmole) was added and the reaction was allowed to warm to RT and stir for 12 hr. The reaction contents were poured into H2O (50 mL) and extracted with EtOAc (2×100 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure and purification on silica (hexanes/EtOAc, 1:1) afforded the title compound (3.14 g, 99%) as a white solid: MS (ES) m/e 291 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic phases were washed sequentially with H2O and brine
  4. dry with materialwere dried over Na2SO4
  5. concentrationConcentration
  6. customunder reduced pressure and purification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-05380ab960ac4cd0a3e440f1d87fab36
Source dataset
uspto-grants-2005_11
Patent number
US06964970B2

Reaction notes

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