Reaction #68324

Reaction equation

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

Compound 8

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

K2CO3

NaOH

3-iodotetrahydrofuran

Compound 29

3-iodotetrahydrofuran

→

title compound

Yield 86.0%

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

Yield 86.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otherpurified by a short silica gel column

Procedure

To a solution of 1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide (Compound 8, 8 mg, 0.039 mmol) in DMF (1.0 ml) was added K2CO3 (13 mg, 0.092 mmol) and catalytic amount of NaOH, 3-iodotetrahydrofuran (Compound 29, 120 mg, crude). The reaction was stirred at room temperature for 2 days, and purified by a short silica gel column to yield the title compound (8 mg, 86%).

Source