Water → 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1261882Notes

Reaction equation

HRID 1261882 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][CH3:37])=[N:34]2)=[CH:29][CH:28]=1.[CH3:38][S:39]([C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1)(=[O:41])=[O:40].CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:27]2[N:35]3[C:30]([CH:31]=[N:32][C:33]([S:36][CH3:37])=[N:34]3)=[CH:29][CH:28]=2)=[CH:44][CH:43]=1)(=[O:41])=[O:40]

Participants

9

Reactant 7

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 312751,4-DioxaneHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667120257-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
80 °C

Procedure

Into a 30 ml, vial, Palladium Acetate (0.11 g, 0.00049 mol) and Triphenylphosphine (0.32 g, 0.0012 mol) were added and purged under an atmosphere of Nitrogen for 5 minutes 1,4-Dioxane (10.8 mL, 0.138 mol) was added and stirred for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.600 g, 0.00246 mol), (4-Methylsulfonylphenyl)boronic acid (0.983 g, 0.00492 mol), N,N-Dimethylformamide (23.7 mL, 0.306 mol) and 1.50 M of Sodium carbonate in Water (4.92 mL, 0.00737 mol) were added, respectively. The reaction mixture was heated at 80° C. overnight. The solvent was removed under vacuum. The solid was washed with DCM. The organic was removed under vacuum. The reaction was purified via ISCO column chromatography with hexane and EtOAc as eluant (0 to 100% EtOAc). The collected fraction afforded 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine a yellow solid (0.63 g, 83%). NMR 1H (DSMO-d6)-9.09 (s, 1H), 8.51 (d, 2H, J=8.48 Hz), 8.05 (d, 2H, J=8.49 Hz), 7.58 (d, 1H, J=4.84 Hz), 7.15 (d, 1H, J=4.84 Hz), 3.27 (s, 3H), 2.62 (s, 3H).

Workup

  1. additionwas added
  2. customThe solvent was removed under vacuum
  3. washThe solid was washed with DCM
  4. customThe organic was removed under vacuum
  5. customThe reaction was purified via ISCO column chromatography with hexane and EtOAc as eluant (0 to 100% EtOAc)

Sources & evidence

ORD record
ord-53d50ee61b0a4fb48f06e487800a24f2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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