Lithium triethylborohydride → 2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one

HRID 2069862Notes

Reaction equation

HRID 2069862 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[C:3]=1[CH:4]=[O:5].[Li+].[B-](CC)(CC)CC>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 594737722-chloro-6-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)benzaldehyde

Product 1

HCID 594737982-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of compound III (0.26 g, 0.76 mmol) in 15 ml dry THF which was cooled at 0° C. in an ice bath, was added a solution of superhydride 1M (1.5 ml, 1.5 mmol) in THF. After stirring for 0.5 hour at 0° C. the reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 0.25 g (96% yield) of IV which was used in the next step without further purification.

Workup

  1. customwas quenched with saturated ammonium chloride
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-746ca1ecb9db4d68a6f9dcb83a0cff55
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…