Methyl iodide → HCID 68510861, compound

HRID 1716574Notes

Reaction equation

HRID 1716574 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]3[OH:23])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].IC.[C:30]([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][CH:11]3[O:23][CH3:30])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68509022HCID 68509022, compound

Product 1

HCID 68510861HCID 68510861, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(5-fluoro-2-methylbenzimidazol-1-yl)-3-hydroxy-Boc-piperidine (205 mg, 0.59 mmol) mmol) in THF (5 mL) and cooled to 0° C. under Ar. NaH (60% oil dispersion; 32 mg, 0.8 mmol) was added and the reaction mixture was stirred for 15 minutes. Iodomethane (0.8 mmol) was then added. After stirring for 3 hours at rt the reaction mixture was poured into saturated NaHCO3 and extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure yielded crude product from which 4-(5-fluoro-2-methylbenzimidazol-1-yl)-3-methoxy-Boc-piperidine (191 mg, 89%) was isolated as a waxy solid.

Workup

  1. stirringAfter stirring for 3 hours at rt the reaction mixture
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-c6721ad5f8ae4ffcb1ac297c1280cce9
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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