Methyl iodide → HCID 86718138, compound

HRID 2205152Notes

Reaction equation

HRID 2205152 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([O:28]C)=[O:27])=[CH:21][CH:20]=3)=[CH:12][CH:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CI>C1COCC1>[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][CH:20]=3)=[CH:14][CH:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86718139HCID 86718139, compound

Product 1

HCID 86718138HCID 86718138, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60 mg, 2.50 mmol, 5.60 equiv) was added to a solution of methyl 3-(4-(t-butoxycarbonyl)phenyl)-2-phenylquinoxaline-6-carboxylate (200 mg, 0.42 mmol, 1.00 equiv, 95%) in THF (10 mL) at 0° C. under an inert atmosphere and stirred for 1 h. A solution of CH3I (125 mg, 0.88 mmol, 2.00 equiv) in THF (1 mL) was added dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction was quenched by the addition of water. The pH value of the solution was adjusted to 3-4 with 1N HCl. The resulting mixture was concentrated under vacuum, yielding 213.5 mg (crude) of 3-(4-(t-butoxycarbonyl)phenyl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. stirringwith stirring at 0° C
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. customThe reaction was quenched by the addition of water
  4. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-93e181b54d03450c9dcd3e5c5c8e0a48
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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