Ethanol → HCID 71203615, compound

HRID 1844553Notes

Reaction equation

HRID 1844553 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[CH:22]=[C:23]([C:29]2[S:33][C:32]([C:34]([O:36][CH3:37])=[O:35])=[C:31]([CH3:38])[C:30]=2[CH3:39])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(O)C>C1(C)C=CC=CC=1>[CH3:28][O:27][C:26]1[C:25]([C:8]2[CH:9]=[CH:10][C:5]([S:2](=[O:4])(=[O:3])[NH2:1])=[CH:6][CH:7]=2)=[CH:24][C:23]([C:29]2[S:33][C:32]([C:34]([O:36][CH3:37])=[O:35])=[C:31]([CH3:38])[C:30]=2[CH3:39])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 71185516HCID 71185516, compound

Product 1

HCID 71203615HCID 71203615, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
97.5 °C

Procedure

4-aminosulfonylbenzene boronic acid (0.54 g, 2.68 mmol) and potassium carbonate (0.67 g, 4.86 mmol) were added to the solution of methyl 5-(3-bromo-4-methoxyphenyl)-3,4-dimethylthiophene-2-carboxylate (step-4, 0.9 g, 2.43 mmol) in a mixture of toluene:ethanol (5:20 ml) in a tube at 25° C. Nitrogen gas was bubbled through reaction mixture for 15 minutes. Tetrakis(triphenylphosphine)(0) palladium (0.14 g, 0.12 mmol) was added to the reaction mixture under nitrogen atmosphere and tube was sealed. The reaction mixture was heated at 95-100° C. for 1 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and filtered through celite. The celite cake was washed with ethyl acetate (30 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product. The crude product so obtained was purified by column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound 9e (0.23 g, 21.2%).

Workup

  1. customat 25° C
  2. customNitrogen gas was bubbled through reaction mixture for 15 minutes
  3. customtube was sealed
  4. temperatureThe reaction mixture was cooled to 25° C.
  5. filtrationfiltered through celite
  6. washThe celite cake was washed with ethyl acetate (30 ml)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customto obtain a crude product
  9. customThe crude product so obtained
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-bcf56bb932d44d5287e94d010e56e262
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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