Methyl iodide → HCID 11429653, compound

HRID 2104496Notes

Reaction equation

HRID 2104496 reaction equation
[C:1]1(/[C:7](/[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])=[N:8]\[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:33]>CN(C=O)C>[CH3:33][O:9]/[N:8]=[C:7](\[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)/[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]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87202177HCID 87202177, compound

Product 1

HCID 11429653HCID 11429653, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone oxime (Example 37, 0.070 g, 0.18 mmol) was taken into DMF (3 mL). Then NaH (0.014 g, 0.36 mmol) was added and stirred for 20 minutes, followed by addition of iodomethane (0.05 mL, 0.72 mmol) and stirring over the weekend. The reaction was quenched with water and extracted with ether. The combined organics were washed with water and dried over magnesium sulfate and concentrated. The resulting material was purified via column chromatography using 5% ethyl acetate in hexane as the eluent to afford 0.063 g (86%) of desired product as a white solid. MS (ESI) m/z 407 ([M+H]+); Anal. Calcd for C24H17F3N2O: C, 70.93; H, 4.22; N, 6.89. Found: C, 70.92; H, 4.19; N, 6.68.

Workup

  1. stirringstirring over the weekend
  2. customThe reaction was quenched with water
  3. extractionextracted with ether
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting material was purified via column chromatography

Sources & evidence

ORD record
ord-775c153df5a34dad9271148e2528008e
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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