Sodium hydride → HCID 22482469, compound

HRID 2182094Notes

Reaction equation

HRID 2182094 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22]Br.[H-].[Na+]>C1COCC1>[CH3:19][C:20]([CH3:24])=[CH:21][CH2:22][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:11]=2[N:10]=[C:9]1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 178423939HCID 178423939, compound

Product 1

HCID 22482469HCID 22482469, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(2,6-difluorophenyl)-4-methylbenzimidazole (Example 13) (0.50 g, 2.05 mmol) and 3,3-dimethylallyl bromide (0.50 mL, 4.34 mmol, 210 M %) dissolved in THF (10 mL) was added NaH (60% dispersion in mineral oil) (0.17 g, 4.25 mmol, 200 M %). After 4 h, the reaction was quenched with MeOH and concentrated. The residue was redissolved in dichloromethane, washed with water and NaCl (sat. aq.), dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography eluting with 2% MeOH/CH2Cl2 and recrystallized from hexane to yield white powders of 1-(3,3-dimethylallyl)-2-(2,6-difluorophenyl)-4-methylbenzimidazole (0.40 g, 1.28 mmol, 63% yield). M.p. 78-79° C. 1H-NMR (200 MHz, CD2Cl2): 7.52 (m, 1H, H4″), 7.26-7.02 (m, 5H, H5,6,7,3″,5″), 5.18 (t, J=6.8 Hz, 1H, H2′), 4.62 (d, J=6.8 Hz, 2H, H1′), 2.64 (s, 3H, CH3), 1.64 (s, 3H, CH3), 1.57 (s, 3H, CH3).

Workup

  1. customthe reaction was quenched with MeOH
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with water and NaCl (sat. aq.)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography
  9. washeluting with 2% MeOH/CH2Cl2
  10. customrecrystallized from hexane

Sources & evidence

ORD record
ord-247d69e2628646b6a6482094ee4252e8
Source dataset
uspto-grants-2005_05
Patent number
US06894068B2

Reaction notes

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