Water → 3-bromo-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

HRID 240842Notes

Reaction equation

HRID 240842 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=1.O>CN(C=O)C>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[CH:10][CH:11]=2)[N:6]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:29][CH3:30])[N:24]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 669549173-bromo-6-(3-nitrophenyl)-1H-indole

Product 1

HCID 509915433-bromo-1-(2-(methylthio)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indoleYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 38 mg, 0.946 mmol) was added to a mixture solution of 3-bromo-6-(3-nitrophenyl)-1H-indole (100 mg, 0.315 mmol) in anhydrous DMF (2 mL) at room temperature. 10 minutes later, 4-chloro-2-(methylthio)pyrimidine (44 μL, 0.378 mmol) was added. After stirring at room temperature for 2 hours, water was added. Thus produced solid was filtered and dried. The target compound (140 mg) was obtained as white solid.

Workup

  1. filtrationThus produced solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-3c6d137dde7c43b2b3e276e2165818c6
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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