Hydrochloric Acid → HCID 58022184, compound

HRID 578782Notes

Reaction equation

HRID 578782 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:28])([CH3:27])[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[O:18])[CH:12]=[CH:13][C:14]=1[F:15])=O)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>>[NH2:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:28])([CH3:27])[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[O:18])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68996014HCID 68996014, compound

Product 1

HCID 58022184HCID 58022184, compoundYield 87.3%

Procedure

A mixture of 1-(2-methoxyphenyl)-2-methyl-1-propanone (0.58 g), 4-bromo-2-(tert-butoxycarbonylamino)-1-fluoro -benzene (0.94 g), palladium(II) acetate (37 mg), tri(tert -butyl)phosphine tetrafluoroborate (47 mg) and sodium tert-butoxide (0.78 g) in tetrahydrofuran (10 mL) was stirred at 60° C. under an argon atmosphere overnight. To the reaction mixture was added water, and the mixture was stirred for 10 minutes. The mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=95/5−85/15) to give 2-[3-(tert-butoxycarbonylamino)-4-fluorophenyl]-1-(2-methoxyphenyl)-2-methyl-1-propanone (0.91 g). To the obtained 2-[3-(tert-butoxycarbonylamino)-4-fluorophenyl]-1-(2-methoxyphenyl)-2-methyl-1-propanone (0.34 g) was added hydrochloric acid (4 mol/L ethyl acetate solution, 3 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give the title compound (0.22 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b9253cd4585c43328a4087dd9fe739d4
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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