Ethanol → 2-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1261909Notes

Reaction equation

HRID 1261909 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1.Br[C:27]1[N:35]2[C:30]([CH:31]=[N:32][C:33]([S:36]([CH3:38])=[O:37])=[N:34]2)=[CH:29][CH:28]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41](B(O)O)[CH:40]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:38][S:36]([C:33]1[N:32]=[CH:31][C:30]2=[CH:29][CH:28]=[C:27]([C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)[N:35]2[N:34]=1)=[O:37]

Participants

10

Reactant 7

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 312751,4-DioxaneHCID 27343783-Pyridinylboronic acidHCID 580713077-Bromo-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667112752-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazineYield 64%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a round bottom flask, Palladium Acetate (0.052 g, 0.00023 mol) and Triphenylphosphine (0.076 g, 0.00029 mol) were dissolved in dioxane (3.5 mL, 0.043 mol) and the mixture was allowed to stir at room temperature for 10 minutes. DMF (5 mL), 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (0.300 g, 0.00115 mol) was then added and the reaction was again allowed to stir for 10 minutes. [B] 3-Pyridylboronic acid (0.284 g, 0.00231 mol) was added followed by 0.9 M of Sodium carbonate in water (1 mL, 0.001 mol) and Ethanol (3.5 mL, 0.060 mol). The reaction mixture was then heated at 80° C. overnight. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over sodium sulfate. The solid was filtered and washed. The solvent was removed under vacuum. The reaction mixture was purified by ISCO column chromatography with DCM and methanol as eluant (0 to 10%). The collected fractions afforded 2-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.19 g, 61%). LCMS (E/I+) 259.8 (M+H)

Workup

  1. stirringto stir for 10 minutes
  2. temperatureThe reaction mixture was then heated at 80° C. overnight
  3. customThe reaction was partitioned with water and DCM
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solid was filtered
  8. washwashed
  9. customThe solvent was removed under vacuum
  10. customThe reaction mixture was purified by ISCO column chromatography with DCM and methanol as eluant (0 to 10%)

Sources & evidence

ORD record
ord-f3b27b356876470b8e3f4de607c19267
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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