Ethanol → HCID 68285965, compound

HRID 1518708Notes

Reaction equation

HRID 1518708 reaction equation
[Br:1][C:2]1[C:6]([N:7]([CH3:9])[CH3:8])=[C:5](Br)[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(O)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=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>[Br:1][C:2]1[C:6]([N:7]([CH3:9])[CH3:8])=[C:5]([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 68286493HCID 68286493, compound2×

Product 1

HCID 68285965HCID 68285965, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Ethyl 3,5-dibromo-4-(dimethylamino)thiophene-2-carboxylate (compound 34c, 3.0 g, 8.40 mmol) in a mixture of toluene:ethanol (5 ml:30 ml) was added (4-chlorophenyl)boronic acid [1.44 g, 9.24 mmol] and potassium carbonate (2.32 g, 16.80 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) (0.48 g, 0.42 mmol) under nitrogen atmosphere and the reaction mixture was heated at about 95 to 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 was then washed with ethyl acetate (50 ml). The filtrate so obtained was then concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 12% ethyl acetate in hexanes as an eluent to obtain the title compound (2.5 g, 76.56%).

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 ethyl acetate (50 ml)
  4. customThe 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-43dcf41c011d4584b3b317352e616735
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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