Sodium borohydride → Methyl 4-cyclopropyl-2-methyl-5-(5-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)benzoate

HRID 1487972Notes

Reaction equation

HRID 1487972 reaction equation
[I-].[CH:2]1([C:5]2[CH:10]=[C:9]([CH3:11])[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[C:16]2[NH:25][C:19]3[CH:20]=[N+:21]([CH3:24])[CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[CH:2]1([C:5]2[C:6]([C:16]3[NH:25][C:19]4[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:18]=4[N:17]=3)=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([CH3:11])[CH:10]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 900303632-(2-Cyclopropyl-5-(methoxycarbonyl)-4-methylphenyl)-5-methyl-3H-imidazo[4,5-c]pyridin-5-ium iodide2×

Product 1

HCID 90020876Methyl 4-cyclopropyl-2-methyl-5-(5-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a mixture of 2-(2-cyclopropyl-5-(methoxycarbonyl)-4-methylphenyl)-5-methyl-3H-imidazo[4,5-c]pyridin-5-ium iodide (compound 87.3, 300 mg, 0.67 mmol) and NaBH4 (1.42 g, 37.5 mmol) in methanol (30 mL). The resulting mixture was stirred for 4 h at room temperature, then concentrated under reduced pressure. The residue was diluted with EtOAc (120 mL) and the mixture was washed with brine (2×40 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with EtOAc/MeOH (20/1) as the eluent to yield 170 mg (78%) the title compound as a light yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (120 mL)
  4. washthe mixture was washed with brine (2×40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography with EtOAc/MeOH (20/1) as the eluent

Sources & evidence

ORD record
ord-518e1c81f9c24045bfaafeda3c48494a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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