Cesium carbonate → HCID 86730165, compound

HRID 1850129Notes

Reaction equation

HRID 1850129 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([C:18]2[N:23]=[C:22]([N:24]3[C@@H:28]([CH:29]([CH3:31])[CH3:30])[CH2:27][O:26][C:25]3=[O:32])[CH:21]=[CH:20][N:19]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH:33]1([C:39]([NH2:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:33]1([C:39]([NH:41][C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([C:18]3[N:23]=[C:22]([N:24]4[C@@H:28]([CH:29]([CH3:31])[CH3:30])[CH2:27][O:26][C:25]4=[O:32])[CH:21]=[CH:20][N:19]=3)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=2)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14283CyclohexanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86730162HCID 86730162, compound

Product 1

HCID 86730165HCID 86730165, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

In a 5 ml microwave reaction vial was added tert-butyl (S)-1-(4-bromophenyl)ethyl(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)carbamate (101 mg, 0.2 mmol), cyclohexanecarboxamide (30 mg, 0.24 mol), cesium carbonate (91 mg, 0.28 mmol), XANTPHOS (7 mg, 0.012 mmol, strem chemicals), and Pd2(dba)3 (4 mg, 0.02 mmol). The vial was sealed, evacuated and purged with dry nitrogen three times before adding dioxane (1.6 mL). The reaction mixture was heated to 100° C. for 16 hours in an oil bath. After cooling the reaction was diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to give a white solid (65 mg, 58.9% yield).

Workup

  1. customIn a 5 ml microwave reaction
  2. customThe vial was sealed
  3. customevacuated
  4. custompurged with dry nitrogen three times
  5. additionbefore adding dioxane (1.6 mL)
  6. temperatureAfter cooling the reaction
  7. additionwas diluted with EtOAc (10 mL)
  8. washwashed with water (10 mL)
  9. customAfter separation
  10. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  11. dry with materialCombined organics were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%)

Sources & evidence

ORD record
ord-a023f3e3aa92445ba556d4e99befaeec
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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