3,5-Dibromoaniline → HCID 86685631, compound

HRID 2200515Notes

Reaction equation

HRID 2200515 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:9])[CH:8]=1)[NH2:5].C([Sn](CCCC)(CCCC)[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)CCC>C1(C)C=CC=CC=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>[N:16]1[CH:17]=[CH:18][CH:19]=[N:20][C:15]=1[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:15]2[N:16]=[CH:17][CH:18]=[CH:19][N:20]=2)[CH:8]=1)[NH2:5].[Br:9][C:7]1[CH:6]=[C:4]([CH:3]=[C:2]([C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:8]=1)[NH2:5]

Participants

6

Reactant 2

HCID 2215123,5-DibromoanilineHCID 27632512-(Tributylstannyl)pyrimidine

Product 2

HCID 86685631HCID 86685631, compoundHCID 86685632HCID 86685632, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 3,5-dibromoaniline (1.05 g, 4.2 mmol), 2-tributylstannylpyrimidine (5.00 g, 13.6 mmol), Pd(Ph3P)4 (0.97 g, 0.84 mmol) in 60 mL toluene was degassed with argon stream and stirred at 110° C. in argon atmosphere for three days. It was cooled to RT, diluted with EtOAc, filtered through celite, concentrated in vacuo, and subjected to silica flash column to isolate 3,5-di(pyrimidin-2-yl)aniline and 3-bromo-5-(pyrimidin-2-yl)aniline.

Workup

  1. customwas degassed with argon stream
  2. temperatureIt was cooled to RT
  3. additiondiluted with EtOAc
  4. filtrationfiltered through celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d1168dbb5bb4d1db0c081ffec0ae72f
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

Loading…