Dimethylformamide → 6-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

HRID 240844Notes

Reaction equation

HRID 240844 reaction equation
[CH3:1][N:2](C=O)C.[Br:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=3)=[CH:13][CH:14]=2)[N:9]([C:25]2[CH:30]=[C:29](Cl)[N:28]=[CH:27][N:26]=2)[CH:8]=1.Cl.CN.C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=3)=[CH:13][CH:14]=2)[N:9]([C:25]2[N:26]=[CH:27][N:28]=[C:29]([NH:2][CH3:1])[CH:30]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 509915443-bromo-1-(6-chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

Product 1

HCID 509915456-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

DMF (10 mL) was added to a mixture of 3-bromo-1-(6-chloropyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (500 mg, 1.16 mmol), methylamine hydrochloride (393 mg, 5.82 mmol) and potassium carbonate (1.60 g, 11.6 mmol). After stirring at 80° C. for 3 hours and then cooling to room temperature, the reaction solution was added to icy water. After stirring at room temperature for 15 hours, thus produced solid was filtered, washed with water and then dried. The target compound (500 mg) was obtained as yellow solid.

Workup

  1. temperaturecooling to room temperature
  2. stirringAfter stirring at room temperature for 15 hours
  3. filtrationthus produced solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-704253538f7c47de9f37202de6314376
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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