Methyl iodide → HCID 59146136, compound

HRID 1512733Notes

Reaction equation

HRID 1512733 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:24][NH:25]4)=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].I[CH3:38]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])=[CH:24][N:25]4[CH3:38])=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 59146052HCID 59146052, compound

Product 1

HCID 59146136HCID 59146136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 7.47 mg) was added to a solution of 1,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D17) (150 mg) in dry DMF (4 mL) at RT. After stirring for 5 min, iodomethane (0.029 mL) was added. The resulting solution was stirred at RT for 1.2 hours. Another portion of sodium hydride (4 mg) was added. After stirring for 5 min, methyliodide (0.015 mL) was added, and the resulting solution was stirred for 1 hour. DMF was evaporated. EtOAc (50 mL) was added and the resulting solution was washed with aqueous HCl (40 mL), followed by water (100 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-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propanoate (D18) (113 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.38 (15H, m), 2.58 (2H, t), 2.93 (2H, t), 3.85 (3H, s), 4.89 (1H, m), 7.32 (1H, br s), 7.45 (1H, d), 7.75 (2H, m), 8.15 (2H, m), 8.22 (1H, d). MS (ES): C27H30ClN3O4 requires 495; found 496.0 (M+H+).

Workup

  1. stirringThe resulting solution was stirred at RT for 1.2 hours
  2. stirringAfter stirring for 5 min
  3. stirringthe resulting solution was stirred for 1 hour
  4. customDMF was evaporated
  5. additionEtOAc (50 mL) was added
  6. washthe resulting solution was washed with aqueous HCl (40 mL)
  7. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  8. concentrationThe dried solution was concentrated
  9. customThe residue was purified by Biotage (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-6c01cfabc8594608b2666795a858d71b
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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