Nitrogen → HCID 69208499, compound

HRID 269500Notes

Reaction equation

HRID 269500 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH:11]([N:13]1[CH:17]=CN=N1)=C.[CH2:18]([N:20]([CH2:23]C)CC)C.[N:25]#N>CN(C=O)C.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]>[N:6]1([CH:5]=[CH:4][C:8]2[CH:9]=[C:10]3[CH:2]=[CH:3][NH:25][C:17]3=[N:13][CH:11]=2)[CH:23]=[N:20][CH:18]=[N:7]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 7619295-bromo-1H-indazoleHCID 113094741-vinyltriazole

Product 1

HCID 69208499HCID 69208499, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-azaindole (1 g, 5.1 mmol), 1-vinyltriazole (600 mg, 6.3 mmol), and triethylamine (5 mL) was dissolved in DMF (25 mL). The solution was treated with N2 gas and PdCl2(dppf) (250 mg, 0.3 mmol) was added. The reaction was heated with stirring at 120° C. for 16 h and evaporated under vacuum. The residue DMF solution was poured into water, filtered, the solid was washed with ether. After drying on the pump for overnight, the crude solid was used for the next reaction directly (800 mg, 3.8 mmol). MS (ES+): m/e=212.1 (M+H); LC: 2.2 min.

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. customevaporated under vacuum
  4. additionThe residue DMF solution was poured into water
  5. filtrationfiltered
  6. washthe solid was washed with ether
  7. customAfter drying on the pump for overnight
  8. customthe crude solid was used for the next reaction directly (800 mg, 3.8 mmol)
  9. custom2.2 min.

Sources & evidence

ORD record
ord-5d1f4dab7a954c0db72c0030efcaabdd
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

Loading…