Methyl iodide → HCID 5306295, compound

HRID 734672Notes

Reaction equation

HRID 734672 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([O:18][CH3:19])=[O:17])=[CH:4][CH:3]=1.I[CH3:21].[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:21])[C:10]([CH3:15])=[C:9]2[C:16]([O:18][CH3:19])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2727782HCID 2727782, compound

Product 1

HCID 5306295HCID 5306295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 2, Step 1 (1.5 g, 5.70 mmol, 1 equiv) and iodomethane (809 mg, 5.70 mmol, 1 equiv) were dissolved in DMF (20 mL) and cooled to 0° C. To this was added portionwise sodium hydride 60% in mineral oil (228 mg, 5.70 mmol, 1 equiv) and warmed to room temperature over 1 h. The reaction was quenched with water, and extracted with EtOAc. The organic phase was concentrated in vacuo. The product was obtained as a light yellow oil (1.58 g, quant.). MS (ES+) m/e 278 [M+H]+.

Workup

  1. temperaturewarmed to room temperature over 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. concentrationThe organic phase was concentrated in vacuo
  5. customThe product was obtained as a light yellow oil (1.58 g, quant.)

Sources & evidence

ORD record
ord-9203caa9b285470ea50faf195b706814
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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