Dichloromethane → 3-(3-Hydroxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one hydrochloride

반응식

C[O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:13]2[C:14](=[O:30])[N:15]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:16]=[CH:17][C:12]=2[S:11][CH:10]=1.B(Br)(Br)Br.[OH-].[Na+].C(Cl)[Cl:38]>>[ClH:38].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:13]2[C:14](=[O:30])[N:15]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:16]=[CH:17][C:12]=2[S:11][CH:10]=1

참가 물질

반응물 4

HCID 6344Dichloromethane2회

HCID 14798Sodium Hydroxide

HCID 25134Boron tribromide

HCID 866831393-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one

생성물 1

HCID 866831413-(3-Hydroxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one hydrochloride

실험 절차

To 3-(3-methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one (50.0 mg, 0.121 mmol) in DCM (20 mL) was added 1M BBr3 in DCM (0.363 mmol, 91 mg). The reaction mixture was stirred for 2 h under nitrogen. The reaction mixture was poured onto water and basified with 1N NaOH, extracted with DCM and dried. The organic phase was concentrated to dryness and the residue was purified by column chromatography (normal phase) on silica using DCM/methanol to give the title compound (13 mg, 0.030 mmol).