Sodium hydride → HCID 14970868, compound

HRID 2104999Notes

Reaction equation

HRID 2104999 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13](Cl)[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.CCOC(C)=O>[CH2:15]([O:14][CH2:13][N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 15193414-Methylbenzimidazole

Product 1

HCID 14970868HCID 14970868, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 171.1 (130 mg, 0.984 mmol) in 3 mL THF at rt, was added sodium hydride (60%, 43 mg, 1.1 mmol). The mixture was stirred 5 min, then BOM-Cl (80%, 0.204 mL, 1.18 mmol) was added. The mixture was stirred at rt for 2 h, then was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 60 mg of Intermediate 171.2.

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. washwashed with H2O (2×) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-fa0ab2e1857044818e912c1a9f17e0f1
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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