Borane → HCID 66616155, compound

HRID 2172156Notes

Reaction equation

HRID 2172156 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[N:16][C:15]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23][CH3:24])=[O:22])=[N:14]2)=[CH:9][CH:8]=1.B>C1COCC1>[N:3]1([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]=[N:16][C:15]([C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[C:21]([O:23][CH3:24])=[O:22])=[N:14]3)=[CH:11][CH:12]=2)[CH2:2][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 66616195HCID 66616195, compound

Product 1

HCID 66616155HCID 66616155, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-{1-[4-(2-oxo-pyrrolidin-1-yl)-phenyl]-1H-[1,2,4]triazol-3-yl}-benzoate (278 mg, 0.77 mmol) in THF (5 mL) is treated with borane.tetrahydrofuran complex (3.85 mmol) at ambient temperature. The resulting solution is stirred for 16 h, and quenched by the addition of 6N aq. HCl. After being allowed to stir for 30 min, the mixture is made basic with the addition of 1N aq. sodium hydroxide solution. The mixture is partially evaporated until a precipitate formed, which is collected by filtration, washed with water, and dried under vacuum to afford 226 mg (84%) of methyl 3-[1-(4-pyrrolidin-1-yl-phenyl)-1H-[1,2,4]triazol-3-yl]-benzoate.

Workup

  1. customat ambient temperature
  2. customquenched by the addition of 6N aq. HCl
  3. stirringto stir for 30 min
  4. additionthe mixture is made basic with the addition of 1N aq. sodium hydroxide solution
  5. customThe mixture is partially evaporated until a precipitate
  6. customformed
  7. filtrationwhich is collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e9bc0f78bdc34857ac27b7fde1f2c4db
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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