Potassium Carbonate → HCID 60169458, compound

HRID 1518743Notes

Reaction equation

HRID 1518743 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].Br[C:18]1[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[C:20]([C:27]2[C:36]3[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=3[C:30]([S:37](=[O:40])(=[O:39])[NH2:38])=[CH:29][CH:28]=2)[C:19]=1[CH3:41]>C1(C)C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[S:22][C:21]([C:23]([O:25][CH2:26][CH3:11])=[O:24])=[C:20]([C:27]3[C:36]4[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=4[C:30]([S:37](=[O:40])(=[O:39])[NH2:38])=[CH:29][CH:28]=3)[C:19]=2[CH3:41])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 68285498HCID 68285498, compound

Product 1

HCID 60169458HCID 60169458, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

(4-chlorophenyl)boronic acid [0.027 g, 0.17 mmol] and potassium carbonate (0.043 g, 0.31 mmol) were added to a solution of methyl 5-bromo-4-methyl-3-(4-sulfamoyl-5,6,7,8-tetrahydronaphthalen-1-yl)thiophene-2-carboxylate (59d, 0.07 g, 0.16 mmol) in a mixture of 1 ml toluene and 4 ml ethanol at 25° C. A nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis (triphenylphosphine)palladium(0) (0.009 g, 0.008 mmol) under nitrogen atmosphere and the reaction mixture was heated at a temperature of about 95° C. to about 100° C. for 3 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite, the celite cake washed with 10 ml ethyl acetate. The combined filtrate so obtained was then concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 30% ethyl acetate in hexanes as an eluent to obtain the title compound (0.027 g, 35.0%).

Workup

  1. customA nitrogen gas was bubbled through reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washthe celite cake washed with 10 ml ethyl acetate
  4. customThe combined filtrate so obtained
  5. concentrationwas then concentrated under reduced pressure
  6. customto obtain a crude product, which
  7. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-218ac8df66d9482a8b241e6e1b90de2c
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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