Ethanol → Tert-butyl 2-(benzamido)-4-(benzothiophen-5-yl)benzoate

HRID 1673456Notes

Reaction equation

HRID 1673456 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.C(=O)([O-])O.[Na+].C(O)C.[C:19]([NH:27][C:28]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:19]([NH:27][C:28]1[CH:40]=[C:39]([C:2]2[CH:3]=[CH:4][C:5]3[S:9][CH:8]=[CH:7][C:6]=3[CH:10]=2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:31])(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 67342196HCID 67342196, compound

Product 1

HCID 67342435Tert-butyl 2-(benzamido)-4-(benzothiophen-5-yl)benzoateYield 57.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

48 mg of 5-bromobenzothiophene, 40 mg of sodium hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of water and 11 mg of tetrakis(triphenylphosphine)palladium(0) were added to 1.6 mL of toluene solution containing 80 mg of tert-butyl 2-(benzamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 5 hours. Ethyl acetate and water were added after the reaction mixture was cooled to room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane; ethyl acetate=20:1] to obtain 47 mg of tert-butyl 2-(benzamido)-4-(benzothiophen-5-yl)benzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 5 hours
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with a saturated sodium chloride aqueous solution
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane; ethyl acetate=20:1]

Sources & evidence

ORD record
ord-eca8bca40d0f44b2829ab67a1304d871
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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