Methyl iodide → HCID 20781268, compound

HRID 2181270Notes

Reaction equation

HRID 2181270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32]I>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:16][CH2:15][CH:14]([N:17]([CH3:32])[S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10434562HCID 10434562, compound

Product 1

HCID 20781268HCID 20781268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The product of Example 1 (52 mg, 0.11 mmol) in tetrahydrofuran (3 ml), cooled to 0° C. was treated with sodium hydride (11 mg, 0.28 mmol) After 10 minutes methyl iodide was added (70 μL, 1.1 mmol) and the reaction heated to 50° C. for 4 hours, then extracted into ethyl acetate and washed with H2O, dried (MgSO4) and evaporated. Product was purified by chromatography (25% ethyl acetate/hexane). 1H NMR (400 MHz, CDCl3) δ 7.36-7.26 (4H, m), 7.04-7.01 (2H, m), 6.79-6.71 (1H, m), 3.91-3.84 (1H, m), 3.24-3.19 (2H, d, broad), 2.91 (3H, s), 2.86 (3H, s), 2.64-2.57 (2H, dd, J=12.5, J=3.8), 2.06-2.01 (2H, m), 1.85-1.76(2H, m). m/z=500, 502 [MNa]+

Workup

  1. additionwas added (70 μL, 1.1 mmol)
  2. extractionextracted into ethyl acetate
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customProduct was purified by chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6e73749e71c24bbbac8fb6df6b68f116
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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