Methyl iodide → HCID 67025232, compound

HRID 1512727Notes

Reaction equation

HRID 1512727 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:28]=3[NH:27][CH:26]=[C:25]4[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4].IC.[CH3:40]COC(C)=O>CN(C=O)C>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:28]=3[N:27]([CH3:40])[CH:26]=[C:25]4[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67094388HCID 67094388, compound

Product 1

HCID 67025232HCID 67025232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 9.14 mg) was added to a solution of 1,1-dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D9) (120 mg) in dry DMF (5 mL) at RT. After stirring for 5 min, iodomethane (0.032 mL) was added. The resulting solution was stirred at RT for 15 min, then 1 hour more. EtOAc (50 mL) was added and the resulting solution was washed with saturated aqueous sodium bicarbonate solution (50 mL), followed by water (50 mL). The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was purified by Biotage (25% EtOAc in hexane) to afford 1,1-dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propanoate (D10) (60 mg) as a pale yellow oil. MS (ES): C28H30N4O4 requires 486; found 487.0 (M+H+).

Workup

  1. stirringThe resulting solution was stirred at RT for 15 min
  2. custom1 hour
  3. washthe resulting solution was washed with saturated aqueous sodium bicarbonate solution (50 mL)
  4. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  5. concentrationThe dried solution was concentrated
  6. customThe residue was purified by Biotage (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-b3010794a2ba41a68a4908ef368fdebb
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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