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With boron trifluoride diethyl etherate; In toluene; at 20.0℃; for 24.0h;
3-Chloro-5-iodobenzoic acid (D52, 4.72 g, 16.71 mmol) in dichloromethane (16.71 ml.) was added to a stirring solution of 1 ,1-dimethylethyl 2,2,2-trichloroethanimidoate (7.30 g, 33.4 mmol) in toluene (33.4 ml.) at room temperature under argon. Boron trifluoride etherate (0.334 ml_, 2.64 mmol) was then added to the mixture and left to stir for 18 hours. 1 ,1-Dimethylethyl 2,2,2-trichloroethanimidoate (7.30 g, 33.4 mmol) was added and the solution allowed to stir for another 6 hours. Solid sodium bicarbonate was added to the reaction mixture which was then filtered through silica <n="64"/>and eluted with dichloromethane. The crude material (10.6 g) was then purified by flash chromatography (eluting with dichloromethane) to afford the title compound as a white solid.1H NMR delta (DMSOd6): 1.54 (9H, s), 7.85 (1 H, dd), 8.1 1-8.13 (2H, m)
3-chloro-5-iodobenzoic acid methyl ester[ No CAS ]
[ 289039-25-4 ]
Yield
Reaction Conditions
Operation in experiment
Water (20 ml.) was added to methyl 3-chloro-5-iodobenzoate (5 g, 16.86 mmol) and lithium hydroxide monohydrate (1.769 g, 42.2 mmol) in tetrahydrofuran (183 ml.) and the solution was stirred for ca. 1 hour at room temperature. The volume was reduced by ca. 50% and water was then added and the pH adjusted to about 4. The product was extracted into ethyl acetate (x3), the organics combined, washed with brine, dried over magnesium sulfate and then concentrated in vacuo to give the title compound. 1H NMR delta (DMSOd6): 7.89 (1 H, dd), 8.12 (1 H, t), 8.16 (1 H, t), 13.6 (1 H, br s).
tert-butyl N-(3-chloro-5-iodophenyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70.3%
To a solution of 3-chloro-5-iodo-benzoic acid (3 g, 10.6 mmol, 1 eq) in 30 mL of toluene was added dropwise DPPA (2.9 g, 10.6 mmol, 2.3 mL, 1 eq) and TEA (1.1 g, 10.6 mmol, 1.5 mL, 1 eq) at 25C. After addition, the mixture was stirred at this temperature for 1 hour and 80C for 1 hour. And then 2-methylpropan-2-ol (944.7 mg, 12.8 mmol, 1.2 mL, 1.2 eq) was added dropwise. The resulting mixture was stirred at 110C for 12 hours. Then it was partitioned between 10 mL of sat. NaHCCL and 10 mL of ethyl acetate. The organic phase was separated, washed with 6 mL of sat. NaHCCL, 5 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, eluting with a gradient of Petroleum ether : Ethyl acetate = 100: 1 to 50: 1) to give 2.6 g of compound 2 (7.8 mmol, 70.3 % yield) as a yellow oil.
With diphenylphosphoranyl azide; triethylamine; at 20 - 80℃; for 13h;
To a solution of 3-chloro-5-iodo-benzoic acid (4.5 g, 15.9 mmol, 1 eq) in 45 mL of t- BuOH was added dropwise DPPA (6.6 g, 23.9 mmol, 5.2 mL, 1.5 eq), TEA (2.4 g, 23.9 mmol, 3.3 mL, 1.5 eq) at 20C. After addition, the mixture was stirred at this temperature for 1 hr, and then warmed to 80C and stirred for another 12 hrs. After reaction, it was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (Si02, eluting with a gradient of petroleum ether : ethyl acetate =1 :0 to 1 :0) to give 2.7 g of compound 3 (7.7 mmol, 48.5% yield) as a yellow oil.
1-(5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-yl)piperazine trifluoroacetic acid[ No CAS ]
1-[(3-chloro-5-iodophenyl)carbonyl]-4-{5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-yl}piperazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
To a solution of 1-(5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-yl)piperazine, trifluoroacetic acid (550 mg, 1.66 mmol) in DMF (5 mL) was added triethylamine (0.92 mL, 6.62 mmol) and stirred for 10 minutes at r.t., followed by the addition of <strong>[289039-25-4]3-chloro-5-iodobenzoic acid</strong> (468 mg, 1.66 mmol) and HATU (944 mg, 2.48 mmol). The mixture was then stirred for 17 h at the same temperature. The reaction mixture was diluted with EtOAc (50 mL), and water (50 mL). The solid part was filtered and washed with EtOAc and dried in vacuo providing the title compound (710 mg, 89%) as an off white solid. MS (ESI): m/z = 482.6 [M+H]+
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