Methyl iodide → HCID 66914315, compound

HRID 2104605Notes

Reaction equation

HRID 2104605 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:32]I>CN(C=O)C>[CH3:32][N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][CH:16]=[CH:15][C:14]=2[C:26]([F:29])([F:27])[F:28])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66913289HCID 66913289, compound

Product 1

HCID 66914315HCID 66914315, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N,4-diphenyl-8-(trifluoromethyl)quinoline-3-carboxamide, (0.150 g, 0.382 mmol), whose preparation is described in Example 368, in DMF (20 mL) is added sodium hydride (0.010 g, 0.421 mmol). After stirring in an ice bath for 1 h, methyl iodide (0.027 mL, 0.421 mmol) is added drop wise and the reaction mixture is removed from the ice bath and stirred 2 h. The reaction mixture is partitioned between ethyl acetate and water and the aqueous layer is extracted with ethyl acetate. The combined extracts are washed with water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:4 ethyl acetate:hexanes to afford the title compound as a white solid (0.147 g, 96%). mp 188-190° C.; MS (ESI) m/z 407; HRMS: calcd for C24H17N2F3O+H, 407.13712; found (ESI, [M+H]+), 407.1361.

Workup

  1. customthe reaction mixture is removed from the ice bath
  2. stirringstirred 2 h
  3. customThe reaction mixture is partitioned between ethyl acetate and water
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. washThe combined extracts are washed with water, brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe extracts are concentrated
  8. customthe residue is chromatographed with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-046a59c20b3c46dbaa7c7a1c21a64fb5
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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