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

HRID 240866Notes

Reaction equation

HRID 240866 reaction equation
CN(C=O)C.Br[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:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[CH:26]=2)[CH:8]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C>[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=4)=[CH:13][CH:14]=3)[N:9]([C:25]3[N:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[CH:26]=3)[CH:8]=2)=[CH:45][CH:44]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 509915456-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509919276-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

DMF (5 mL) was added to a mixture of 6-(3-bromo-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (300 mg, 0.710 mmol), K3PO4 (452 mg, 2.13 mmol) and 4-methoxyphenylboronic acid (215 mg, 1.41 mmol) and then the dissolved gas was removed. After adding Pd(PPh3)4 (123 mg, 0.11 mmol), the mixture was stirred at 120° C. for 2 hours. After adding ethyl acetate and water and then filtering using a diatomite pad, the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:4→1:1). The target compound was obtained as white solid.

Workup

  1. customthe dissolved gas was removed
  2. filtrationfiltering
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe collected organic layer was washed with brine
  6. concentrationconcentrated under reduced pressure
  7. dry with materialby drying with anhydrous magnesium sulfate
  8. customThe residue was purified by chromatography (silica gel, EA:Hx=1:4→1:1)
  9. customThe target compound was obtained as white solid

Sources & evidence

ORD record
ord-a6ee5f8b9491480597495e20344b4a7b
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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