Ethanol → HCID 66710816, compound

HRID 1261922Notes

Reaction equation

HRID 1261922 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.Br[C:26]1[N:34]2[C:29]([CH:30]=[N:31][C:32]([S:35][CH3:36])=[N:33]2)=[CH:28][CH:27]=1.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([O:47][CH3:48])=[C:42](B(O)O)[CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(O)C.[Cl-].[Na+]>C([O-])(=O)C.[Pd+2].ClC1C=CC(OC)=C(C2N3C(C=NC(SC)=N3)=CC=2)C=1.C([O-])(=O)C>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([O:47][CH3:48])=[C:40]([C:26]2[N:34]3[C:29]([CH:30]=[N:31][C:32]([S:35][CH3:36])=[N:33]3)=[CH:28][CH:27]=2)[CH:39]=1

Participants

10

Reactant 8

HCID 702EthanolHCID 962WaterHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66710816HCID 66710816, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 86661664HCID 86661664, compoundCatalyst

Procedure

7-(5-Chloro-2-methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine Palladium Acetate (0.37 g, 0.0016 mol) and Triphenylphosphine (0.54 g, 0.0020 mol) were dissolved in Tetrahydrofuran (25 mL, 0.31 mol) and the mixture was allowed to stir at room temperature for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (2.00 g, 0.00819 mol) was then added and the reaction was again allowed to stir for 10 minutes. 5-Chloro-2-methoxyphenyl boronic acid (3.05 g, 0.0164 mol) was added followed by 0.9 M of Sodium carbonate in water (20 mL, 0.02 mol) and Ethanol (25 mL, 0.43 mol). The reaction mixture was then heated at 80° C. and was allowed to stir overnight. The reaction mixture was then poured over saturated sodium chloride, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 1.16 g of 7-(5-Chloro-2-methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid.

Workup

  1. stirringto stir for 10 minutes
  2. temperatureThe reaction mixture was then heated at 80° C.
  3. stirringto stir overnight
  4. extractionorganics were extracted with ethyl acetate/dichloromethane
  5. dry with materialCombined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-a7cc333df32a4325b95d91a180f24eb3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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