Iodoethane → HCID 68870576, compound

HRID 1723668Notes

Reaction equation

HRID 1723668 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][NH:15][C:16](=[O:17])[C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:18]1[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[H-].[Na+].[Br-].[Li+].I[CH2:31][CH3:32]>COCCOC.CN(C)C=O.O>[CH2:31]([N:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:4]=3)=[CH:9][N:10]=[C:11]2[C:16]1=[O:17])[CH3:32]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 68871217HCID 68871217, compound

Product 1

HCID 68870576HCID 68870576, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 2′-fluoro-5′-(8-oxo-7,8-dihydroimidazo[1,2-a]pyrazin-3-yl)biphenyl-2-carbonitrile (50.0 mg, 0.51 mmol) in 1,2-dimethoxyethane (2 ml) and N,N-dimethylformamide (0.5 ml) was treated with sodium hydride (6.4 mg of a 60% dispersion in mineral oil, 0.16 mmol). After stirring at ambient temperature for 10 min, lithium bromide (26.3 mg, 0.30 mmol) was added, and stirring continued for 15 min. Iodoethane (24.2 μl, 0.30 mmol) was added and the solution heated at 65° C. for 18 h. Water (15 ml) was added and the resulting mixture was extracted with dichloromethane (3×10 ml). The combined organic layers were washed with water (10 ml), saturated sodium chloride solution (10 ml), dried over anhydrous magnesium sulphate then concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 2% methanol in dichloromethane. Crystallisation from methanol afforded the title compound as a white solid (23.9 mg, 44%): δH (500 MHz, CDCl3) 1.38 (3H, t, J 7.2), 4.06 (2H, q, J 7.2), 6.72 (1H, d, J 5.9), 7.39 (1H, t, J 9.3), 7.44 (1H, d, J 5.9), 7.53-7.61 (5H, m), 7.69-7.73 (1H, m), 7.84 (1H, d, J 7.3); m/z (ES+) 359 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 15 min
  3. temperaturethe solution heated at 65° C. for 18 h
  4. extractionthe resulting mixture was extracted with dichloromethane (3×10 ml)
  5. washThe combined organic layers were washed with water (10 ml), saturated sodium chloride solution (10 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationthen concentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel
  9. washeluting with 2% methanol in dichloromethane
  10. customCrystallisation from methanol

Sources & evidence

ORD record
ord-1a2bf47c99f84ab29ec22d98d49922e1
Source dataset
uspto-grants-2009_02
Patent number
US07485640B2

Reaction notes

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