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Cesium carbonate → HCID 70818497, compound

HRID 591056
Notes
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Reaction equation

HRID 591056 reaction equation
[C:1]([O:5][CH:6]([C:12]1[C:16](B2OC(C)(C)C(C)(C)O2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O[C:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][CH:6]([C:12]1[C:16]([C:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 70818507HCID 70818507, compound

Product 1

HCID 70818497HCID 70818497, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (50 mg, 0.114 mmol), cyclohex-1-en-1-yl trifluoromethanesulfonate (29a) (27.7 mg, 0.120 mmol) and cesium carbonate (112.2 mg, 0.344 mmol) was dissolved in dry N,N-dimethylformamide (570 μL). The solution was degassed under argon and PdCl2(dppf) (5.6 mg, 0.007 mmol) was added. The reaction was heated and shaken at 100° C., for 6.5 hours. The mixture was filtered through Celite®, rinsed with ethyl acetate and dichloromethane. The solution was concentrated in vacuo and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by preparative TLC (cyclohexane/ethyl acetate 90/01) to provide the desired product (30 mg, 0.09 mmol, 75%).

Workup

  1. customThe solution was degassed under argon
  2. temperatureThe reaction was heated
  3. filtrationThe mixture was filtered through Celite®
  4. washrinsed with ethyl acetate and dichloromethane
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude material was purified by preparative TLC (cyclohexane/ethyl acetate 90/01)

Sources & evidence

ORD record
ord-33b3521a957b4920947aa82073769488
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238026B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes