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

HRID 40046Notes

Reaction equation

HRID 40046 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)=[O:19])=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].I[CH:42]1[CH2:46][CH2:45][O:44][CH2:43]1>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH:42]3[CH2:46][CH2:45][O:44][CH2:43]3)[CH:15]=2)[C:10]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)=[O:19])=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 221392643-Iodotetrahydrofuran2×HCID 251607401-Benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide2×

Product 1

HCID 250600001-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(tetrahydrofuran-3-yloxy)-1H-indole-3-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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%).

Workup

  1. custompurified by a short silica gel column

Sources & evidence

ORD record
ord-606c6d932dab47efab400290782fd201
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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