Cesium carbonate → HCID 59532375, compound

HRID 450982Notes

Reaction equation

HRID 450982 reaction equation
[CH2:1]([C@@:4]1([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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>[CH2:1]([C@@:4]1([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 59532386HCID 59532386, compound

Product 1

HCID 59532375HCID 59532375, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Pd(PPh3)2Cl2 (100 mg) was added to the solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(thiophen-2-yl)-1,3-oxazinan-2-one (1.0 g, 2.5 mmol), 4-fluorophenylboronic acid (420 mg, 3.0 mmol) in 1,4-dioxane. Cs2CO3 (5 mL) was slowly added. The mixture was heated to reflux for 2 h. The mixture was quenched with water and separated, extracted with EtOAc twice, dried over anhydrous Na2SO4 and concentrated to afford the residue, which was purified by TLC to give (R)-6-allyl-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(thiophen-2-yl)-1,3-oxazinan-2-one (768 mg, 73%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe mixture was quenched with water
  4. customseparated
  5. extractionextracted with EtOAc twice
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto afford the residue, which
  9. customwas purified by TLC

Sources & evidence

ORD record
ord-e3ed83bce9794956aa7af4997458c97e
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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