Methyl iodide → HCID 69314233, compound

HRID 269960Notes

Reaction equation

HRID 269960 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:23][CH2:22][C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][C:20]=3[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH3:25]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:23][CH2:22][C:13]2[N:14]([CH3:25])[C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][C:20]=3[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69312818HCID 69312818, compound

Product 1

HCID 69314233HCID 69314233, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (80% in oil, 0.0190 g, 0.633 mmol) in dry THF (1 mL), was added a solution of 8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (0.114 g, 0.393 mmol) in THF (4 mL) via cannula. The reaction mixture was allowed to stir at room temperature for 5 min and then iodomethane (0.098 mL, 1.57 mmol) was added. The resulting mixture was stirred for 2 h and then it was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic phase was separated, dried (MgSO4), filtered and concentrated to dryness to give the title compound (0.109 g, 91%) as a yellow oil which was used without further purification. LCMS: m/e 305 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred for 2 h
  2. customit was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2b064108f0be4396b43b990b2a499251
Source dataset
uspto-grants-2008_11
Patent number
US07449476B2

Reaction notes

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