Sodium Bicarbonate → Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

HRID 2191699Notes

Reaction equation

HRID 2191699 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32](Cl)=[O:33])=[CH:24]1.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32]([NH:1][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)=[O:33])=[CH:24]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2776338Benzo(b)thiophene-3-carbonyl chlorideHCID 68958505Tert-butyl 4-amino-2-(4-fluoroanilino)benzoate

Product 1

HCID 68959063Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To dichloromethane 3.0 mL solution of tert-butyl 4-amino-2-(4-fluoroanilino)benzoate 40 mg were added triethylamine 0.064 mL, benzothiophene-3-carbonyl chloride 55 mg and dichloromethane 1.5 mL at room temperature, and it was stirred at same temperature for 2 hours. Aminomethylated-polystyrene 250 mg was added to the reaction mixture, and it was stirred at room temperature for 4 hours. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and insoluble matter was filtrated. The organic layer was separated and collected, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate.

Workup

  1. stirringwas stirred at room temperature for 4 hours
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. customcollected
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-19b302fce4034fc4b65c6e7619158580
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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