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Ethanol → HCID 68285705, compound

HRID 1518709
Notes
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Reaction equation

HRID 1518709 reaction equation
Br[C:2]1[C:6]([N:7]([CH3:9])[CH3:8])=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[S:4][C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(O)C.[S:25]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)(=[O:28])(=[O:27])[NH2:26].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:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[S:4][C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:30][CH:31]=3)[C:6]=2[N:7]([CH3:9])[CH3:8])=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 68285965HCID 68285965, compound2×

Product 1

HCID 68285705HCID 68285705, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Ethyl 3-bromo-5-(4-chlorophenyl)-4-(dimethylamino)thiophene-2-carboxylate (compound 34d, 2.20 g, 5.65 mmol) in a mixture of toluene:ethanol (10 ml:30 ml) was added (4-sulfamoylphenyl)boronic acid (1.25 g, 6.22 mmol) and potassium carbonate (1.56 g, 11.30 mmol) at 25° C. Nitrogen gas was bubbled through the reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.32 g, 0.28 mmol) under nitrogen and the reaction mixture was heated at about 95 to about 100° C. for 16 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 was then washed with ethanol (2×25 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 55% ethyl acetate in hexanes as an eluent to obtain the title compound (2.0 g, 76.05%).

Workup

  1. customNitrogen gas was bubbled through the reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washThe celite cake was then washed with ethanol (2×25 ml)
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. customto obtain a crude product, which
  6. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-5799e5f9cec34367afe5e03639d35250
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09072731B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes