Ethyl Acetate → 6-(6-(4-methoxyphenyl)-1H,1'H-3,6'-biindol-1-yl)-N-methylpyrimidin-4-amine

HRID 2192278Notes

Reaction equation

HRID 2192278 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[N:4]([C:19]2[N:24]=[CH:23][N:22]=[C:21]([NH:25][CH3:26])[CH:20]=2)[CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C(C)(C)OB([C:43]2[CH:51]=[C:50]3[C:46]([CH:47]=[CH:48][NH:49]3)=[CH:45][CH:44]=2)O1.C(OCC)(=O)C>CN(C)C=O.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>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[CH:6]=[C:5]3[C:10]([C:2]([C:43]4[CH:51]=[C:50]5[C:46]([CH:47]=[CH:48][NH:49]5)=[CH:45][CH:44]=4)=[CH:3][N:4]3[C:19]3[N:24]=[CH:23][N:22]=[C:21]([NH:25][CH3:26])[CH:20]=3)=[CH:9][CH:8]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 447548546-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 509915476-(3-bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509910016-(6-(4-methoxyphenyl)-1H,1'H-3,6'-biindol-1-yl)-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6-(3-Bromo-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (50 mg, 0.074 mmol), K3PO4 (47.1 mg, 0.222 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (27 mg, 0.111 mmol) were dissolved in dimethylformamide (2 mL) and then Pd(PPh3)4 (12.83 mg, 0.011 mmol) was added. After stirring at 120° C. for 3 hours, followed by addition of ethyl acetate and water, the reaction solution was filtered using a diatomite pad. The aqueous layer was extracted with ethyl acetate and the collected organic layer was washed with brine and then concentrated under reduced pressure by drying with magnesium sulfate. The residue was purified by chromatography (silica gel, EtOAc:hexane=1:10→1:4→1:2). The target compound was obtained as brown solid.

Workup

  1. filtrationthe reaction solution was filtered
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe collected organic layer was washed with brine
  4. concentrationconcentrated under reduced pressure
  5. dry with materialby drying with magnesium sulfate
  6. customThe residue was purified by chromatography (silica gel, EtOAc:hexane=1:10→1:4→1:2)
  7. customThe target compound was obtained as brown solid

Sources & evidence

ORD record
ord-409471084e4845ada37073f5bd7726e2
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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