Reaction #68401

Reaction equation

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

Compound 125

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

dihydrofuran-3(2H)-one

Compound 129

dihydrofuran-3(2H)-one

NaBH3CN

→

title compound

1-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(tetrahydrofuran-3-ylamino)-1H-indole-3-carboxamide

Solvents

EtOAc

MeOH

Conditions

Workup

1. 1
   Washwashed with aqueous Na2CO3 and brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Procedure

General Procedure T. To a solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide (Compound 125, 15 mg, 0.035 mmol) in MeOH (1 ml) was added dihydrofuran-3(2H)-one (Compound 129, 6.0 mg, 0.069 mmol), NaBH3CN (2.2 mg, 0.035 mmol), and HOAc (1 drop). The reaction was stirred at room temperature for 3 h, diluted with EtOAc, washed with aqueous Na2CO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound.

Source