Water → HCID 136360287, compound

HRID 1262273Notes

Reaction equation

HRID 1262273 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[N:29]2[C:24]([CH:25]=[N:26][C:27]([S:30][CH3:31])=[N:28]2)=[CH:23][CH:22]=1.CC1(C)C(C)(C)OB([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[O:46]C(=O)C)O1.C(=O)([O-])[O-].[Na+].[Na+].O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH3:31][S:30][C:27]1[N:26]=[CH:25][C:24]2=[CH:23][CH:22]=[C:21]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[OH:46])[N:29]2[N:28]=1

Participants

8

Reactant 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27740012-Acetoxyphenylboronic acid pinacol esterHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 136360287HCID 136360287, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a 8-dram vial, Palladium Acetate (0.050 g, 0.022 mol) and Triphenylphosphine (0.16 g, 0.063 mmol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (17.1 mL,) was added and stirred for 10 minutes at room temperature. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.550 g, 2.25 mmol), Acetic acid 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl ester (1.18 g, 4.51 mmol), N,N-Dimethylformamide (34 mL), and 1.50 M of Sodium carbonate in Water (13.5 mL, 0.0203 mol) were added. The reaction was heated at 90° C. for 18 hours. The reaction was partitioned with water and stirred at room temperature for 2 hours. The solid was filtered and washed with water. The resulting yellow solid was dried under vacuum to give 2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (0.53 g, 92%).

Workup

  1. customThe mixture was purged under an atmosphere of Nitrogen for 10 minutes
  2. addition1,4-Dioxane (17.1 mL,) was added
  3. temperatureThe reaction was heated at 90° C. for 18 hours
  4. customThe reaction was partitioned with water
  5. stirringstirred at room temperature for 2 hours
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customThe resulting yellow solid was dried under vacuum

Sources & evidence

ORD record
ord-13663a3ff9e74c70b2f430a6df06014c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…