Lithium borohydride → HCID 67405191, compound

HRID 2101955Notes

Reaction equation

HRID 2101955 reaction equation
[C:1]([C:3]1[C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13](OC)=[O:14])[C:7]([CH3:17])=[CH:6]2)#[N:2].[Li+].[BH4-]>C1COCC1>[OH:14][CH2:13][CH2:12][N:8]1[C:9]2[C:5](=[C:4]([C:18]([F:21])([F:19])[F:20])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[C:7]1[CH3:17]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70985592HCID 70985592, compound

Product 1

HCID 67405191HCID 67405191, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl [5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate (0.200 g, 6.76 mmol) in THF (5 mL) was cooled to 0° C. and treated with LiBH4 (0.51 mL, 2M in THF). After 2 h, the reaction was partitioned between Et2O and water. Drying (Na2SO4), filtration, and concentration was followed by column chromatography (SiO2, hexanes/EtOAc) to afford the title compound (0.137 g): MS (ES) m/z 269 (M+1).

Workup

  1. customthe reaction was partitioned between Et2O and water
  2. customDrying
  3. filtration(Na2SO4), filtration, and concentration

Sources & evidence

ORD record
ord-980a05625379402dbbe8ecdf494ae9e3
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…