Methyl iodide → HCID 66692725, compound

HRID 1048983Notes

Reaction equation

HRID 1048983 reaction equation
[F:1][C:2]1[C:18]([F:19])=[CH:17][C:5]2[N:6]([OH:16])[C:7]([C:9]3[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:22]I>C1COCC1>[F:1][C:2]1[C:18]([F:19])=[CH:17][C:5]2[N:6]([O:16][CH3:22])[C:7]([C:9]3[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66693171HCID 66693171, compound

Product 1

HCID 66692725HCID 66692725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-difluoro-2-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-1-ol 0.15 g, 0.0003 mol) in THF (3.5 ml) was added NaH (0.045 g, 0.0011 mol) at room temperature. After stirring for 5 min at room temperature MeI (0.04 mL, 0.00059 mol) was added in one shot and further stirred for another 1 hr. After the consumption of the starting material (by TLC) the reaction mixture was washed with H2O and extracted with EtOAc (2×30 mL). The organic phase was dried and concentrated under vacuum. The crude was washed with Hexanes and further purified by chromatography (5-40% EtOAc/Hexanes) to give the desired compound 372 as a white solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.28 (s, 1H), 8.62 (s, 1H), 8.24 (s, 1H), 7.58 (s, 1H), 7.32 (s, 1H), 4.06 (s, 3H). MS (M+1): 280, Purity 99.67%.

Workup

  1. additionwas added in one shot
  2. customAfter the consumption of the starting material (by TLC) the reaction mixture
  3. washwas washed with H2O
  4. extractionextracted with EtOAc (2×30 mL)
  5. customThe organic phase was dried
  6. concentrationconcentrated under vacuum
  7. washThe crude was washed with Hexanes
  8. customfurther purified by chromatography (5-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-aea9a952ec1e4a1fb607d513865f0c0e
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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