Methyl iodide → HCID 59497544, compound

HRID 1747367Notes

Reaction equation

HRID 1747367 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24]([CH3:26])=[CH2:25])[C:16]2=[O:27])=[C:12]2[C:8]([C:9]([CH3:29])=[C:10]([CH3:28])[NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH3:32]I.[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24]([CH3:26])=[CH2:25])[C:16]2=[O:27])=[C:12]2[C:8]([C:9]([CH3:29])=[C:10]([CH3:28])[N:11]2[CH3:32])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59497229HCID 59497229, compound

Product 1

HCID 59497544HCID 59497544, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-2,3-dimethyl-1H-indole-6-carboxylic acid methyl ester (107 mg, 0.3 mmol) in THF (10 mL) was added NaH (60% in mineral oil) (22 mg, 0.55 mmol) at 0 C under nitrogen atmosphere. The solution was stirred at the same temperature for 15 minutes. MeI (0.034 mL, 0.55 mmol) was added and the solution was stirred at 0 C for 2 hour. Sat. NH4Cl solution was added and the solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 7-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (100 mg. 90%) as a colorless oil.

Workup

  1. stirringthe solution was stirred at 0 C for 2 hour
  2. extractionthe solution was extracted with EtOAc
  3. dry with materialThe combined organic layer was dried with MgSO4
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-bd5f48d60156407783ce2351eb323ef7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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