Methyl iodide → HCID 86701772, compound

HRID 2174128Notes

Reaction equation

HRID 2174128 reaction equation
[C:1]([CH:3]([C:8]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH3:19])=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:4]([O:6][CH3:7])=[O:5])#[N:2].IC.[C:29](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]([C:8]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH3:19])=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:29])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86701771HCID 86701771, compound

Product 1

HCID 86701772HCID 86701772, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(±)-tert-Butyl 4-(1-cyano-2-methoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 155-C) (1.1 g, 3.07 mmol) was dissolved in acetone (6.14 ml) and then added iodomethane (0.576 ml, 9.21 mmol) followed by potassium carbonate (0.636 g, 4.60 mmol) and stirred at room temperature for 2.5 hours. The reaction was then cooled in an ice bath and quenched with a saturated aqueous solution of ammonium chloride and diluted with DCM. The layers were separated and the organic layer was dried and concentrated to obtain the title compound. MS (ESI+) m/z 373.4 (M+H).

Workup

  1. temperatureThe reaction was then cooled in an ice bath
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. additiondiluted with DCM
  4. customThe layers were separated
  5. customthe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f6a7c07b9b24f5ab142092c406ade42
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…