Water → HCID 18511433, compound

HRID 1370332Notes

Reaction equation

HRID 1370332 reaction equation
[C:1]1([CH:7]([C:9]2[C:18]3[C:13](=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:23]([F:26])([F:25])[F:24])[CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:30].O>C1COCC1>[CH3:30][O:8][CH:7]([C:9]1[C:18]2[C:13](=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:23]([F:26])([F:24])[F:25])[CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9864199HCID 9864199, compound

Product 1

HCID 18511433HCID 18511433, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of α-phenyl-2,8-bis(trifluoromethyl)quinoline-4-methanol (50 mg, 0.13 mmol) in anhydrous THF (4 mL) was treated with NaH (18 mg, 60% dispersion in oil, 0.44 mmol), stirred at room temperature for 2 min, treated with iodomethane (0.8 mL, 1.2 mmol) and stirred for 15 min. The solution was then treated with water (10 mL), extracted with ether (2×10 mL), the extracts washed with water (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (10:1)] to give the title compound (41 mg, 79%) as a pale solid: mp 115-117° C.; IR νmax (liquid film)/cm−1 3070, 2929, 2854, 1589, 1588, 1517, 1491, 1456, 1429, 1378, 1210, 1276, 1211, 1184, 1164, 1129 and 1101; NMR δH (400 MHz, CDCl3) 3.47 (3H, s), 5.90 (1H, s), 7.29-7.35 (5H, m), 7.60-7.64 (1H, t J 8 Hz) and 8.25 (1H, d J 8 Hz).

Workup

  1. stirringstirred for 15 min
  2. extractionextracted with ether (2×10 mL)
  3. washthe extracts washed with water (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2; heptane-EtOAc (10:1)]

Sources & evidence

ORD record
ord-f1340cdf086b4250bed0b2485798f670
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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