Water → 3-bromo-1-(6-chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

HRID 2192252Notes

Reaction equation

HRID 2192252 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:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[CH:25][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:27]2[CH:28]=[C:23]([Cl:22])[N:24]=[CH:25][N:26]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 669549173-bromo-6-(3-nitrophenyl)-1H-indole

Product 1

HCID 509915443-bromo-1-(6-chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indoleYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 114 mg, 2.84 mmol) was added to a mixture solution of 3-bromo-6-(3-nitrophenyl)-1H-indole (450 mg, 1.42 mmol) and 4,6-dichloropyrimidine (212 mg, 1.42 mmol) in anhydrous DMF (10 mL) at room temperature. After stirring at room temperature for 5 hours, followed by addition of ice, the mixture was added to icy water. After stirring at room temperature for 12 hours, the produced solid was filtered, washed with water, and then dried. The target compound (600 mg) was obtained as yellow solid.

Workup

  1. additionfollowed by addition of ice
  2. stirringAfter stirring at room temperature for 12 hours
  3. filtrationthe produced solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5850f35ed29f4cd5a3b87da642c154c7
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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