Ethanol → HCID 58382311, compound

HRID 1628082Notes

Reaction equation

HRID 1628082 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:24])[N:5]2[C:10]3[CH:11]=[CH:12][N:13](S(C4C=CC(C)=CC=4)(=O)=O)[C:9]=3[N:8]=[CH:7][C:6]=12.[CH:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26].CCO.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.[Pd]>[CH3:24][C:4]1[N:5]2[C:10]3[CH:11]=[CH:12][NH:13][C:9]=3[N:8]=[CH:7][C:6]2=[C:2]([C:30]2[CH:31]=[CH:32][C:27]([CH:25]=[O:26])=[CH:28][CH:29]=2)[N:3]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 5910734-Formylphenylboronic AcidHCID 58382162HCID 58382162, compound

Product 1

HCID 58382311HCID 58382311, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave reaction vial containing 3-bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.100 g, 0.247 mmol, Preparation #AB.1), 4-formylphenylboronic acid (0.074 g, 0.493 mmol, Lancaster) and SiliaCat® DPP-Pd (0.031 g, 0.025 mmol, Silicycle) in 1,4-dioxane (1.0 mL) and EtOH (1.0 mL) was added a solution of Cs2CO3 (0.177 g, 0.543 mmol) in water (0.3 mL). The mixture was heated in a microwave at 150° C. for 30 min. The mixture was filtered through a filtration tube with a polyethylene frit, and the resulting solid was rinsed with EtOAc (5 mL). The solid was dissolved in a 9:1 DCM/MeOH solution and filtered. The filtrate was concentrated under reduced pressure followed by drying overnight in a vacuum oven at about 65° C. to give the title compound (0.052 g, 76%): LC/MS (Table 2, Method c) Rf=1.67 min.; MS m/z: 277 (M+H)+.

Workup

  1. customTo a microwave reaction
  2. filtrationThe mixture was filtered through a filtration tube with a polyethylene frit
  3. washthe resulting solid was rinsed with EtOAc (5 mL)
  4. dissolutionThe solid was dissolved in a 9:1 DCM/MeOH solution
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customby drying overnight in a vacuum oven at about 65° C.

Sources & evidence

ORD record
ord-ba4933c574e4483e9347c3c783bdcb91
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…