* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydroxylamine hydrochloride; sodium acetate; In sodium hydroxide; ethanol; water;
Example IV-34 3-(3-bromophenyl)-5-isoxazolamine To a solution of <strong>[70591-86-5]3-(3-bromophenyl)-3-oxopropanenitrile</strong> (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (*1). The organic layer was washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification. LC/MS (method B) 2.21 min, m/z 239, 241 (Br isotopes).
With hydroxylamine hydrochloride; sodium acetate; In NaOH; ethanol; water;
Example IV-34 3-(3-bromophenyl)-5-isoxazolamine To a solution of <strong>[70591-86-5]3-(3-bromophenyl)-3-oxopropanenitrile</strong> (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (*1). The organic layer was washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification. LC/MS (method B) 2.21 min, m/z 239, 241 (Br isotopes).
With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; for 1h;Reflux;
To a solution of <strong>[70591-86-5]3-(3-bromophenyl)-3-oxopropanenitrile</strong> (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (×1). The organic layer was washed (water, brine), dried over Na2SO4and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification.
tert-butyl (3-(3-bromophenyl)isoxazol-5-yl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With dmap; triethylamine In dichloromethane at 20℃; for 1h;
22.1 Step 1. tert-butyl (3-(3-bromophenyl)isoxazol-5-yl)carbamate
Into a 250-mL round-bottom flask, was placed a solution of 3-(3-bromophenyl)- l, 2- oxazol-5-amine (1 g, 4.18 mmol, 1.00 equiv) in dichloromethane (40 mL), Boc20 (1.83 g, 8.38 mmol, 2.00 equiv), triethylamine (1.27 g, 12.55 mmol, 3.00 equiv), 4- dimethylaminopyridine (51.24 mg, 0.42 mmol, 0.10 equiv). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with 2x20 mL of hydrochloric acid (0.5M), dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.42 g (crude) of the title compound as an off-white solid. LC- MS (ES, m/z): 339[M+H]+
With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; zinc In 1-methyl-pyrrolidin-2-one at 160℃; for 4h; Inert atmosphere; Microwave irradiation;
73.a Step a.
A solution of 3-(3-bromophenyl) isoxazol-5-amine (CAS Number 1 19162-52- 6; 0.250 g, 1 .05 mmol) in NMP (10 ml) was degassed for 15 min at rt. Zinc dust (0.034g, 0.52 mmol), zinc cyanide (0.30 g, 2.62 mmol), Pd2(dba)3 (0.190 g, 0.21 mmol) and tri-tert-butylphosphonium tetrafluoroborate (CAS Number 131274-22-1 ; 0.060 g, 0.21 mmol) were added sequentially to the reaction mixture. The reaction mixture was heated under microwave irradiation at 160°C for 4 h. The resulting mixture was poured into water (70 ml) and extracted with EtOAc (2 x 50 ml). The collected organic extracts were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude mass, which was purified by column chromatography (compound eluted at 30% EtOAc in n- hexane) to yielding 3-(5-aminoisoxazol-3-yl)benzonitrile (0.150 g, 0.81 mmol). LCMS: Method C, 1 .770 min, MS: ES+186.1
N-(3-(3-bromophenyl)isoxazol-5-yl)-5-ethyl-2-methoxybenzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
13%
With pyridine at 20℃; for 16h;
75
Example 75: N-(3-(3-bromophenyl)isoxazol-5-yl)-5-ethyl-2- methoxybenzenesulfonamide, 75 A mixture of 5-ethyl-2-methoxylbenzenesulfonyl chloride 119 (0.098 g, 0.418 mmol), pyridine (1 ml.) and 3-(3-bromophenyl)isoxazol-5-amine (0.050 g, 0.209 mmol) was stirred at room temperature for 16 h. The mixtures were diluted with DCM (1 ml.) and washed with 1 M HCI (2 ml_). The aqueous layer was removed and the organic layer was dried to give the crude residue. The product was purified by HPLC to give the title compound (12 mg, 13% yield). LCMS Rt 5.91 min, m/z = 438.8 [M+H]+.
N-(3-(3-bromophenyl)isoxazol-5-yl)benzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With pyridine at 20℃; for 16h;
80
Example 80: N-(3-(3-bromophenyl)isoxazol-5-yl)benzenesulfonamide, 80 A mixture of 3-(3-bromophenyl)isoxazol-5-amine (0.050 g, 0.209 mmol), benzenesulfonyl chloride 1107 (0.040 ml_, 0.314 mmol) and pyridine (1 ml.) was stirred at room temperature for 16 h. The solvent was removed in vacuo to afford a crude residue. This was dissolved in DCM (2 ml.) and 1 M HCI (2 ml.) and filtered through a phase separation cartridge. The crude product was purified by flash chromatography gradient eluting with 100% dichloromethane to 20% MeOH/dichloromethane to give the title compound (66 mg, 84 % yield) LCMS Rt 6.13 min, m/z = 381.4 [M+H]+.
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 20℃; for 32h;
77.a
77a) 3-(3-Benzylphenyl)isoxazol-5-amine, A13 Benzylzinc bromide (0.502 ml_, 0.5 M in THF, 0.251 mmol) was added to a solution of 3-(3- bromo-phenyl)-isoxazol-5-ylamine (0.050 g, 0.209 mmol), Pd(OAc)2 (0.001 g, 0.004 mmol), S-Phos (0.002 g, 0.004 mmol) in THF (2 ml_). The mixture was stirred for 16 h at room temperature. Additional benzylzinc bromide (0.502 ml_, 0.5 M in THF, 0.251 mmol), Pd(OAc)2 (0.003 g, 0.012 mmol) and S-Phos (0.009 g, 0.024 mmol) were added and the mixture continued stirring for 16 h. The mixture was quenched with saturated NH4CI (3 ml.) and diluted in EtOAc (5 ml_). The organic layer was isolated and washed with water (2 x 5 ml_). The organic layer was dried (magnesium sulfate), filtered and reduced in vacuo to afford A13 as a brown oil (0.052 g, 99% crude yield). The product was used without further purification. LCMS Rt 5.42 min, m/z = 251.5 [M+H]+.
N-(3-(3-benzylphenyl)isoxazol-5-yl)-3,4-dimethylbenzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 32 h / 20 °C
2: pyridine / 16 h / 20 °C
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 20℃; for 32h;
78.a
Example 78: 3,4-dimethyl-N-(3-(3-phenethylphenyl)isoxazol-5- yl)benzenesulfonamide, 78 a) 3-(3-Phenethylphenyl)isoxazol-5-amine, A14 Phenethylzinc bromide (0.502 ml_, 0.5 M in THF, 0.251 mmol) was added to a solution of 3-(3-bromophenyl)-isoxazol-5-ylamine (0.050 g, 0.209 mmol), Pd(OAc)2 (0.001 g, 0.004 mmol), S-Phos (0.002 g, 0.008 mmol) in THF (2 ml_). The mixture was stirred for 16 h at room temperature. Phenethylzinc bromide (0.502 ml_, 0.5 M in THF, 0.251 mmol),Pd(OAc)2 (0.003 g, 0.012 mmol) and S-Phos (0.009 g, 0.024 mmol) were added and the reaction continued stirring for another 16 h. The mixture was quenched with saturated NH4CI (3 ml.) and diluted in EtOAc (5 ml_). The organic layer was isolated and washed with water (2 x 5 ml_). The organic layer was dried (magnesium sulfate), filtered and reduced in vacuo to afford A14 as a brown oil (0.046 g, 83% crude yield). A14 was used without further purification. LCMS Rt 5.60 min, m/z = 265.7 [M+H]+.
3,4-dimethyl-N-(3-(3-phenethylphenyl)isoxazol-5-yl)benzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 32 h / 20 °C
2: pyridine / 16 h / 20 °C
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