Methyl iodide → HCID 10344345, compound

HRID 1768477Notes

Reaction equation

HRID 1768477 reaction equation
[F:1][CH:2]([F:32])[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[CH2:10][N:9]1[C:21]([N:23]([CH3:25])[CH3:24])=[O:22].[H-].[Na+].[CH3:35]I>C1COCC1>[F:32][CH:2]([F:1])[CH2:3][N:4]([CH3:35])[CH2:5][CH2:6][CH2:7][C:8]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[CH2:10][N:9]1[C:21]([N:23]([CH3:25])[CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10433843HCID 10433843, compound

Product 1

HCID 10344345HCID 10344345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 35 mg (0.08 mmol) of amine 19-4 in THF was added 22 mg (0.55 mmol) of NaH (60% dispersion in oil) and 24 μL (0.39 mmol) of MeI. After stirring for 1 h, the reaction was quenched with water and partitioned with EtOAc, washed with brine, dried over MgSO4, concentrated by rotary evaporation, and the residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 19-5 a colorless gum. Data for 19-5: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.2 (s, 1H), 5.8 (m, 1H), 4.9 (m, 1H), 4.7 (m, 1H), 3.0 (m, 1H), 2.8-2.7 (m, 8H), 2.55 (m, 2H), 2.35 (s, 3H), 2.1 (m, 1H), 1.5 (m, 2H) ppm. HRMS (MS) calc'd M+H for C25H29F4N3O: 464.2320. Found: 464.2320.

Workup

  1. customthe reaction was quenched with water
  2. custompartitioned with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customthe residue was purified by column chromatography on silica gel with EtOAc/hexanes
  7. customto provide 19-5 a colorless gum

Sources & evidence

ORD record
ord-a3eaa5a7ea8d4fe8b7216028a2c61f0a
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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