Methyl iodide → HCID 88380020, compound

HRID 976449Notes

Reaction equation

HRID 976449 reaction equation
[CH3:1][N:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=2)[CH:5]([CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)[NH:4][C:3]1=[O:33].[H-].[Na+].[CH3:36]I>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]([CH2:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:10]=2)[CH:5]([CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)[N:4]([CH3:36])[C:3]1=[O:33]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 88379947HCID 88379947, compound

Product 1

HCID 88380020HCID 88380020, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 1 (0.5 g) in tetrahydrofuran (5 ml) was treated with sodium hydride (43 mg of a 60% dispersion in oil) under a nitrogen atmosphere with stirring. After 5 minutes methyl iodide (0.28 g) was added and stirring continued for 2 hours. The reaction was diluted with ethyl acetate, washed with water, dried and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether and crystallised from ethyl acetate-petroleum ether to give the title compound, mp 202°-205° C.; found: C, 59.88; H, 4.23; N, 8.42. C24H21F6N3O requires C, 59.88; H, 4.40; N, 8.73.

Workup

  1. stirringstirring
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether
  6. customcrystallised from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-fd6d8b9814994bd292a86489f8c610bb
Source dataset
uspto-grants-1997_03
Patent number
US05612362

Reaction notes

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