Cesium fluoride → HCID 118079138, compound

HRID 1485756Notes

Reaction equation

HRID 1485756 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([C:27](=[O:29])[CH3:28])[C@@H:10]([CH3:30])[CH2:9]1)=[O:7].[N:31]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.[F-].[Cs+]>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:36]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:37])[CH:16]=2)[N:11]([C:27](=[O:29])[CH3:28])[C@@H:10]([CH3:30])[CH2:9]1)=[O:7]

Participants

4

Reactant 3

HCID 25953Cesium fluorideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 123316250HCID 123316250, compound

Product 1

HCID 118079138HCID 118079138, compoundYield 8%

Conditions

Temperature
80 °C

Procedure

A 1.5 mL reaction vial was charged with (S)-1-(4-(furan-2-carbonyl)-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinoxalin-1 (2H)-yl)ethanone (0.2 M in 1,4-dioxane, 150 μL, 0.03 mmol), and pyrrolidine-1-carbonyl chloride (4 mg, 0.030 mmol). Cesium fluoride was then added (5 mg, 0.030 mmol) and the reaction mixture was purged with nitrogen. Bis(triphenylphosphine)palladium(II) dichloride (1 mg, 0.0015) was then added, and the reaction was purged with nitrogen and heated overnight at 80° C. on a heater shaker. The reaction was diluted with ethyl acetate (0.5 mL) washed with brine (0.5 mL). The aqueous layer was separated and washed with ethyl acetate (1 mL) and the combined organic layers were concentrated under a stream of nitrogen. The crude product was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford (S)-1-(4-(furan-2-carbonyl)-2-methyl-6-(pyrrolidine-1-carbonyl)-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.0009 g, 8%). MS (ESI, pos. ion) m/z 382.

Workup

  1. customA 1.5 mL reaction
  2. customthe reaction mixture was purged with nitrogen
  3. additionBis(triphenylphosphine)palladium(II) dichloride (1 mg, 0.0015) was then added
  4. customthe reaction was purged with nitrogen
  5. additionThe reaction was diluted with ethyl acetate (0.5 mL)
  6. washwashed with brine (0.5 mL)
  7. customThe aqueous layer was separated
  8. washwashed with ethyl acetate (1 mL)
  9. concentrationthe combined organic layers were concentrated under a stream of nitrogen
  10. customThe crude product was purified by mass
  11. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-67e0bc9249e440b2b9b16d3b6bfab07d
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

Loading…