Cesium fluoride → HCID 118046777, compound

HRID 595888Notes

Reaction equation

HRID 595888 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1([CH3:21])[C:14](C)(C)OB(CC(C)=C)O1.[F-].[Cs+]>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].C(Cl)Cl>[CH3:14][C:10](=[CH2:9])[CH2:21][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 5995392-Amino-5-bromopyrazineHCID 111377474,4,5,5-Tetramethyl-2-(2-methylprop-2-en-1-yl)-1,3,2-dioxaborolane

Product 1

HCID 118046777HCID 118046777, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopyrazin-2-amine (1 g, 5.75 mmol) in was added 4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane (1.360 g, 7.47 mmol), PdCl2(dppf)-DCM adduct (0.469 g, 0.575 mmol), CsF (2.62 g, 17.24 mmol), purge though nitrogen. The reaction mixture was stirred at 100° C. in oil bath for 3h. The reaction mixture was partitioned between EtOAc and water. The organic was washed with brine, dried and concentrated. The residue was dissolved in 1N HCl (10 mL) The aqueous layer was back extracted with EtOAc, The aqueous was then neutralized to pH=8, then extracted by EtOAc 3 times. The organic was then dried and concentrated. The crude product was used in next step reaction. LCMS (m/z): 150.5 (MH+), 0.28 min.

Workup

  1. custompurge though nitrogen
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washThe organic was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 1N HCl (10 mL) The aqueous layer
  7. extractionwas back extracted with EtOAc
  8. extractionextracted by EtOAc 3 times
  9. customThe organic was then dried
  10. concentrationconcentrated
  11. customThe crude product was used in next step reaction
  12. custom150.5 (MH+), 0.28 min.

Sources & evidence

ORD record
ord-61db27e3ede045af8d1af619304602db
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…