Methyl iodide → HCID 58566577, compound

HRID 2069704Notes

Reaction equation

HRID 2069704 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[C:15]([CH3:24])[C:14]=3[CH3:25])[CH:10]=1)[NH:7][C:6]([CH3:27])([CH3:26])[CH2:5]2.[H-].[Na+].[CH3:30]I>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[C:15]([CH3:24])[C:14]=3[CH3:25])[CH:10]=1)[N:7]([CH3:30])[C:6]([CH3:27])([CH3:26])[CH2:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58566390HCID 58566390, compound

Product 1

HCID 58566577HCID 58566577, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (310) (20 mg, 0.05 mmol) in DMF (3 mL) was added sodium hydride (4.3 mg, 2 eq.) and the reaction mixture was stirred at 40° C. for 1 hour. The solution was warmed to room temperature, an excess of methyl iodide was added and the reaction was sealed and warmed to 40° C. overnight. The reaction was quenched with water and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to afford compound (311). 1H NMR (400 MHz, CDCl3) δ 6.97 (d, J=8.2 Hz, 1H), 6.93-6.91 (m, 2H), 6.78 (d, J=8.2 Hz, 1H), 4.99 (s, 2H), 3.83 (s, 2H), 3.68 (s, 3H), 2.94-2.90 (m, 2H), 2.56-2.52 (m, 2H), 2.20 (s, 3H), 2.12 (s, 3H), 1.54 (s, 6H). LC-MS ESI m/z: found 384.5 (M−H)−.

Workup

  1. temperatureThe solution was warmed to room temperature
  2. customthe reaction was sealed
  3. temperaturewarmed to 40° C. overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate (2×20 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9f00852de212486696bb8810dd44abdb
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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