Lithium borohydride → HCID 89874234, compound

HRID 715421Notes

Reaction equation

HRID 715421 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14](OCC)=[O:15])[N:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[BH4-].[Li+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[N:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:13])[F:11]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 89874066HCID 89874066, compound

Product 1

HCID 89874234HCID 89874234, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 5-methyl-6-(2,2,2-trifluoroethoxy)pyridazine-3-carboxylate (1.70 g, 6.43 mmol, Step-2 of Amine-48) in THF (32 mL) is added a solution of lithium borohydride in THF (3 M, 3.22 mL, 9.65 mmol) at 0° C. After stirring at 0° C. for 4 hours, the reaction is quenched with saturated aqueous sodium bicarbonate solution (50 mL). The mixture is filtered through a pad of Celite, and the filtrate is extracted with EtOAc (200 mL). The separated organic layer is washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:2) to give 1.22 g (85% yield) of the title compound as white solid.

Workup

  1. customthe reaction is quenched with saturated aqueous sodium bicarbonate solution (50 mL)
  2. filtrationThe mixture is filtered through a pad of Celite
  3. extractionthe filtrate is extracted with EtOAc (200 mL)
  4. washThe separated organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:2)

Sources & evidence

ORD record
ord-e364d3ec9177481a9f196fdf7fa53186
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…