Methyl iodide → HCID 68960321, compound

HRID 269386Notes

Reaction equation

HRID 269386 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=[C:13]2[OH:24].[C:25]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:22])([F:21])[F:23])[CH:14]=[C:13]2[O:24][CH3:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178516131HCID 178516131, compound

Product 1

HCID 68960321HCID 68960321, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 6-(1-benzofuran-2-yl)-4-hydroxy-2-(trifluoromethyl)-quinoline (1.33 g, 4.04 mmol) in DMF (40 mL) at room temperature was added K2CO3 (0.670 g, 4.85 mmol) followed by methyl iodide (0.276 mL, 4.44 mmol) drop-wise. The reaction mixture was stirred for 4 hours then concentrated and the residue was diluted with EtOAc (200 mL). The organic layer was washed with H2O (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (Na2SO4). After concentration, the residue was purified on a Biotage Flash 40 apparatus (5-15% EtOAc:petroleum ether) to afford the product (0.930 g) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 344. 1H NMR (500 MHz, DMSO-d6): δ 8.67 (s, 1H), 8.46 (d, 1H, J=9.1 Hz), 8.19 (d, 1H, J=9.1 Hz), 7.68-7.79 (m, 3H), 7.48 (s, 1H), 7.40 (t, 1H, J=7.8 Hz), 7.32 (t, 1H, J=7.8 Hz), and 4.26 ppm (s, 3H).

Workup

  1. concentrationthen concentrated
  2. additionthe residue was diluted with EtOAc (200 mL)
  3. washThe organic layer was washed with H2O (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was purified on a Biotage Flash 40 apparatus (5-15% EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-1c92c5d6857d4cc4853f1a6bfcad535f
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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