Bicarbonate Ion → Tert-butyl 2-(benzamido)-4-(2-fluorophenyl)benzoate

HRID 1673470Notes

Reaction equation

HRID 1673470 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[Na].C(=O)([O-])O.[C:16]([NH:24][C:25]1[CH:37]=[C:36](Br)[CH:35]=[CH:34][C:26]=1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>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.C1(C)C=CC=CC=1.C(O)C>[C:16]([NH:24][C:25]1[CH:37]=[C:36]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:35]=[CH:34][C:26]=1[C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

9

Reactant 5

HCID 769Bicarbonate IonHCID 516892Sodium BicarbonateHCID 27343542-Fluorophenylboronic acid2×HCID 5360545SodiumHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67343885Tert-butyl 2-(benzamido)-4-(2-fluorophenyl)benzoate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

56 mg of 2-fluorophenylboronic acid, 0.10 g of sodium, hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of wafer and 23 mg of tetrakis(triphenylphosphine)palladium(0) were added to 2.1 mL of toluene solution containing 0.15 g of tert-butyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux for 2 hours, lifter the reaction mixture was cooled to room temperature, 17 mg of 2-fluorophenylboronic acid and 23 mg of tetrakis(triphenylphosphine )palladium(0) were added and she resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, toluene and a saturated sodium hydrogen carbonate aqueous solution were added. 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 [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=10:1] to obtain tert-butyl 2-(benzamido)-4-(2-fluorophenyl)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours, lifter the reaction mixture
  3. customshe resulting mixture
  4. temperaturewas heated
  5. temperatureto reflux for 2 hours
  6. temperatureAfter the reaction mixture was cooled to room temperature
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washed with a saturated sodium chloride aqueous solution
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-0189ab6c830a48ffa547043f3fc0ad5a
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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