1,2-Dichloroethane → Ethyl 3-{3-chloro-5-[5-(3-chloro-4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl}propanoate

温度

80 °C

3-Chloro-4-hydroxybenzoic acid (commercial) (240 mg, 1.40 mmol) in dry DMF (8 ml) was treated with EDC (292 mg, 1.52 mmol) and HOBt (208 mg, 1.52 mmol) and stirred for 5 minutes. Added ethyl 3-{3-chloro-5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D96) (432 mg, 1.40 mmol) and stirred at RT for 30 minutes. The reaction mixture was heated at 80° C. for 7 hours. Added EtOAc (70 ml) and washed with water (70 ml), sat. aq, sodium hydrogen carbonate (70 ml) and water (70 ml). Dried over MgSO4 and evaporated off the solvent. The residue was subjected to chromatography using a biotage (EtOAc/hexane 1:2) to obtain the title compound as 200 mg of white solid. δH (400 MHz, d6-DMSO) 1.10 (3H, t), 2.91 (2H, t), 4.04 (2H, q), 4.50 (2H, t), 7.67-7.70 (2H, m), 7.75 (1H, s), 7.80-7.81 (2H, m), 7.94 (1H, dd), 8.22-8.25 (1H, m), 10.95 (1H, broad s). MS (ES) C21H1735Cl2N3O4 requires 445; found 446 (MH+).

1. washAdded EtOAc (70 ml) and washed with water (70 ml)
2. dry with materialDried over MgSO4
3. customevaporated off the solvent

ORDレコード

ord-20defe00f96442328a941b6183503f89

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08101775B2