Cesium carbonate → HCID 89813267, compound

HRID 1051894Notes

Reaction equation

HRID 1051894 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14].O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.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].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>[Br:7][C:5]1[N:6]=[C:2]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])[S:3][CH:4]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 126652-PiperidoneHCID 312751,4-DioxaneHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 89813267HCID 89813267, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2,4-dibromothiazole (2.0 g, 8.23 mmol) and piperidine-2-one (0.816 g. 8.23 mmol) were added to seal tube containing 1,4 dioxane (15 ml). Cesium carbonate (4.02 g, 12.35 mmol) and xantphos (027 g, 0.412 mmol) were added, the nitrogen gas was bubbled through reaction mixture for 15 minutes and tris(dibenzylideneacetone)dipalladium(0) (0.151 g, 0.165 mmol) was added under nitrogen and the tube was sealed. The reaction mixture was heated at 120° C. for 3 hr under stirring. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and diluted with water (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extract was dried over sodium sulfate filtered and concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 15% ethyl acetate in hexanes as an eluent to obtain the title compound (1.2 g, 55.8%). MS: m/z 262 (M+1).

Workup

  1. customto seal tube
  2. customthe nitrogen gas was bubbled through reaction mixture for 15 minutes
  3. customthe tube was sealed
  4. customThe progress of reaction
  5. temperatureThe reaction mixture was cooled to 25° C.
  6. extractionextracted with ethyl acetate (3×100 ml)
  7. extractionThe combined organic extract
  8. dry with materialwas dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto obtain a crude product
  12. customwhich was purified by flash column chromatography

Sources & evidence

ORD record
ord-4befddd06e894c6c82f553875b5b66d2
Source dataset
uspto-grants-2016_07
Patent number
US09388196B2

Reaction notes

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