Methyl iodide → HCID 68931011, compound

HRID 32118Notes

Reaction equation

HRID 32118 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:24]>CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[N:7]([CH:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]#[N:19])=[CH:15][CH:16]=2)[O:11][CH2:10][CH2:9]1)[CH3:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68925518(7-cyano-chroman-4-yl)-carbamic Acid tert-butyl Ester

Product 1

HCID 68931011HCID 68931011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (7-cyano-chroman-4-yl)-carbamic acid tert-butyl ester (769 mg, 2.81 mmol, 1.0 eq), NaH (Aldrich, 449 mg (60% by weight), 11.2 mmol, 4.0 eq) in DMF (15 mL) was stirred at RT for 3 h. Iodomethane (Aldrich, 1.99 g, 14.1 mmol, 5.0 eq) was added slowly. The resulting mixture was stirred at RT for 21 h. The reaction was quenched with saturated NH4Cl (40 mL) DMF was removed with a rotary evaporator at 70° C. The crude was diluted with H2O (100 mL), extracted with EtOAc (80 mL×4). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-15% EtOAc-Hexane) afforded the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 289 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at RT for 21 h
  2. customThe reaction was quenched with saturated NH4Cl (40 mL) DMF
  3. customwas removed with a rotary evaporator at 70° C
  4. additionThe crude was diluted with H2O (100 mL)
  5. extractionextracted with EtOAc (80 mL×4)
  6. washThe extract phase was washed with saturated NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8bc73af271684d68940453aa67a60c38
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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