Water → HCID 118079525, compound

HRID 1485701Notes

Reaction equation

HRID 1485701 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](C(=O)C(F)(F)F)[C@@H:7]([CH3:18])[CH2:6][N:5]2[C:19]([C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)=[O:20].[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].C(=O)(O)[O-].[Na+].O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[C:19]([N:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:33]3[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=3)[CH:3]=2)[NH:8][C@@H:7]([CH3:18])[CH2:6]1)=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 118080017HCID 118080017, compound

Product 1

HCID 118079525HCID 118079525, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 100 mL round bottomed flask fitted with a nitrogen inlet was charged with (S)-1-(6-bromo-4-(furan-2-carbonyl)-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)-2,2,2-trifluoroethanone (0.626 g, 1.5 mmol), 1,4-dioxane (15 mL), 4-(methylsulfonyl)phenylboronic acid (0.360 g, 1.8 mmol), and sodium bicarbonate as a 1M solution in water (4.5 mL, 4.5 mmol). The reaction mixture was purged with nitrogen. Bis(triphenylphosphine)palladium(II) dichloride (0.01 M solution in DMF, 7.5 mL, 0.075 mmol) was added, and the reaction mixture was purged with nitrogen and heated to 80° C. overnight. The reaction was diluted with ethyl acetate (30 mL) and washed with brine (15 mL). The aqueous layer was separated and washed with ethyl acetate (30 mL) and the combined organic layers were concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 1:1 hexanes-ethyl acetate) to afford (S)-furan-2-yl(3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-yl)methanone (0.33 g, 55% yield) as a viscous yellow oil. MS (ESI, pos. ion) m/z 397 [M+1]+.

Workup

  1. customA 100 mL round bottomed flask fitted with a nitrogen inlet
  2. customThe reaction mixture was purged with nitrogen
  3. customthe reaction mixture was purged with nitrogen
  4. additionThe reaction was diluted with ethyl acetate (30 mL)
  5. washwashed with brine (15 mL)
  6. customThe aqueous layer was separated
  7. washwashed with ethyl acetate (30 mL)
  8. concentrationthe combined organic layers were concentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (eluting with 1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-6df34b65b61a4375a81133be60a863a3
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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