تفاعل #69708

معادلة التفاعل

2,3-dihydro-1H-isoindole

HOBt

5-bromo-2,4-dihydroxy-benzoic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

المردود 44.0%

(5-Bromo-2,4-dihydroxy-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

المردود 44.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed in vacuo
2. 2
   غسيلwashed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine
3. 3
   تجفيفthen dried (MgSO4)
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was triturated with methanol

الإجراء التجريبي

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1H, s), 7.36 (1H, br.s), 7.35 (1H, s), 7.28 (3H, br.s), 6.59 (1H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+332/334.

المصدر