Methyl iodide → 3-Fluoro-4-[methyl-(3-methylbenzimidazol-5-yl)amino]benzonitrile

HRID 59948Notes

Reaction equation

HRID 59948 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[CH:18][N:19]([CH3:20])[C:15]=2[CH:14]=1)[C:7]#[N:8].CI.[CH2:25](Cl)Cl>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N:12]([CH3:25])[C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[CH:18][N:19]([CH3:20])[C:15]=2[CH:14]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 1182353423-Fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile

Product 1

HCID 1182353223-Fluoro-4-[methyl-(3-methylbenzimidazol-5-yl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (7.14 mmol) was added to a solution of 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile (2.38 mmol) in THF (10 mL) at 0° C. The mixture was stirred for 30 min. MeI (4.76 mmol) was added and the mixture was stirred at room temperature during 3 h. The mixture was diluted (DCM), washed (H2O) and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound C).

Workup

  1. stirringthe mixture was stirred at room temperature during 3 h
  2. washwashed (H2O)
  3. concentrationconcentrated
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-ecb244f0f8264134b3ef06d927c8f33c
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

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