Methyl iodide → HCID 23559704, compound

HRID 1775202Notes

Reaction equation

HRID 1775202 reaction equation
[O:1]=[C:2]1[C:14]2[C:13]3[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH3:19]C(C)([O-])C.[K+].CI>C1COCC1>[CH3:19][N:7]1[C:6]2[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:14]=2[C:13]2[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11368514methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23559704HCID 23559704, compoundYield 178.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate (0.27 g, 1 mmol) in THF (5 ml) at 0° C. under N2 was added potassium t-butoxide (0.12 g, 1.05 mmol). The reaction mixture was stirred for 30 minutes followed by the addition of methyl iodide (0.76 g, 5.0 mmol). After 3 hours, the reaction mixture was concentrated to a residue and partitioned between EtOAc (40 ml) and 1N HCl (5 ml). The layers were shaken and separated. The organic layer was washed with 1N HCl (2×80 ml) and brine (2×10 ml), dried over Na2SO4, filtered, and concentrated to give a solid (0.46 g). The solid was used in the next step without further purified. 1H NMR (DMSO-d6) δ 7.35-7.39 (m, 2H), 7.29 (t, 1H, J=7.2 Hz), 4.01 (s, 3H), 3.72 (s, 3H), 2.93-2.95 (m, 2H), 2.54-2.56 (m, 2H), and 2.23-2.26 (m, 2H). MS (ESI) m/e [M+1]+ 258.0

Workup

  1. waitAfter 3 hours
  2. concentrationthe reaction mixture was concentrated to a residue
  3. custompartitioned between EtOAc (40 ml) and 1N HCl (5 ml)
  4. stirringThe layers were shaken
  5. customseparated
  6. washThe organic layer was washed with 1N HCl (2×80 ml) and brine (2×10 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2770031834843d9a5ba2454fb0bc9e2
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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