Potassium Carbonate → 6-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amine

HRID 2276768Notes

Reaction equation

HRID 2276768 reaction equation
Br[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([F:19])=[C:14](B(O)O)[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C:2]2[N:7]=[N:6][C:5]([NH2:8])=[N:4][CH:3]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10856974(5-Bromo-2-fluorophenyl)boronic acidHCID 153325646-Bromo-1,2,4-triazin-3-amine

Product 1

HCID 674534646-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amineYield 41%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

6-Bromo-1,2,4-triazin-3-amine (9.1 g, 40.8 mmol), 5-bromo-2-fluorophenylboronic acid (98.9 g, 40.8 mmol), (dppf)PdCl2 (3.0 g, 4.0 mmol), nitrogen-sparged dioxane (81.6 mL), and aq. 2 N K2CO3 (17 mL) were combined and heated in a round bottom flask at 90° C. for 4 h. The hot mixture was filtered through a pad of celite and diluted with EtOAc and washed with water. Concentration followed by trituration with DCM afforded a tan solid (4.5 g), m/z=269.0 [M+H].

Workup

  1. filtrationThe hot mixture was filtered through a pad of celite
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. concentrationConcentration

Sources & evidence

ORD record
ord-ed26deeb77da45faa742c0064f9851bd
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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