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

HRID 240858Notes

Reaction equation

HRID 240858 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][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[N:9]([C:24]2[N:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[CH:25]=2)[CH:8]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N+:40]([C:43]1[CH:44]=[C:45](B(O)O)[CH:46]=[CH:47][CH:48]=1)([O-:42])=[O:41]>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>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:12]2[CH:11]=[C:10]3[C:15]([C:7]([C:47]4[CH:46]=[CH:45][CH:44]=[C:43]([N+:40]([O-:42])=[O:41])[CH:48]=4)=[CH:8][N:9]3[C:24]3[N:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[CH:25]=3)=[CH:14][CH:13]=2)=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 509915476-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509918416-(6-(4-methoxyphenyl)-3-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineYield 31.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

DMF (5 mL) was added to a mixture of 6-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (200 mg, 0.49 mmol), K3PO4 (312 mg, 0.885 mmol) and 3-nitrophenylboronic acid (123 mg, 0.74 mmol) and then the dissolved gas was removed. After adding Pd(PPh3)4 (85 mg, 0.075 mmol), the mixture was stirred at 100° C. for 4 hours. After adding ethyl acetate and water and 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 (70 mg) 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)

Sources & evidence

ORD record
ord-0b0f8948fe03407c95ea23444b30a990
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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