Ethanol → HCID 89813354, compound

HRID 1051895Notes

Reaction equation

HRID 1051895 reaction equation
Br[C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[S:5][CH:6]=1.C(O)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[N:3]=[C:4]([N:7]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]3=[O:13])[S:5][CH:6]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 89813267HCID 89813267, compound2×

Product 1

HCID 89813354HCID 89813354, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(4-bromothiazol-2-yl)piperidin-2-one (Step-1 of compound 10, 1.0 g, 3.83 mmol) in a mixture of toluene:ethanol (10 ml: 30 ml) were added (4-chlorophenyl) boronic acid (0.72 g, 4.60 mmol) and potassium carbonate (1.06 g, 7.66 mmol) at 25° C. in a tube, the nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (0.44 g, 0.38 mmol) under nitrogen the tube was sealed. The reaction mixture was heated at 100° C. for 10 hr with stirring. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and filtered through celite. The residue was washed with ethyl acetate (2×30 ml). The filtrate was concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 10% ethyl acetate in hexanes as an eluent to obtain the title compound (0.80 g, 71.4%). MS: m/z 293 (M+1).

Workup

  1. customthe nitrogen gas was bubbled through reaction mixture for 15 minutes
  2. customwas sealed
  3. customThe progress of reaction
  4. temperatureThe reaction mixture was cooled to 25° C.
  5. filtrationfiltered through celite
  6. washThe residue was washed with ethyl acetate (2×30 ml)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto obtain a crude product
  9. customwhich was purified by flash column chromatography

Sources & evidence

ORD record
ord-dd22d17ff7284b3ba0314c50e22a0d30
Source dataset
uspto-grants-2016_07
Patent number
US09388196B2

Reaction notes

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