Dimethylformamide → HCID 86698654, 화합물

반응식

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[C:23]#[N:24])[NH:19][CH:18]=[CH:17]3)=[CH:10][CH:9]=1.CN([CH:28]=[O:29])C>>[CH:28]([C:17]1[C:16]2[C:20](=[CH:21][C:22]([C:23]#[N:24])=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=3)[CH:15]=2)[NH:19][CH:18]=1)=[O:29]

참가 물질

반응물 3

HCID 6228Dimethylformamide2회

HCID 24813Phosphorus oxychloride2회

HCID 86698653HCID 86698653, 화합물

생성물 1

HCID 86698654HCID 86698654, 화합물수율 51%

실험 절차

Phosphorous oxychloride (84.3 mg, 0.54 mmol) was added to DMF (1 mL) at 0° C. and the reaction mixture was stirred for 15 minutes. To this solution was added 5-(4-methoxy-phenyl)-1H-indole-6-carbonitrile (150.0 mg, 0.60 mmol) in DMF (1 mL) and the reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, treated with additional phosphorous oxychloride (84.3 mg, 0.54 mmol) and stirred at 45° C. for an additional hour. The reaction mixture was cooled to room temperature, and quenched with water (10 mL). The solution was concentrated in vacuo, and the residue was partitioned between water (10 mL) and EtOAc (10 mL). The layers were separated and the organic layer was concentrated in vacuo. The crude material was slurried in CH2Cl2, and the resulting solid was filtered and air dried to give the title compound (85 mg, 51% yield). MS (ES−) 275.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 12.63 (br. s., 1H), 10.00 (s, 1H), 8.58 (d, J=3.12 Hz, 1H), 8.17 (s, 1H), 8.10 (s, 1H), 7.51 (d, J=8.59 Hz, 2H), 7.09 (d, J=8.80 Hz, 2H), 3.83 (s, 3H).