Phosphorus oxychloride → 7-Chloro-6-iodothieno[3,2-b]pyridine

반응식

[I:1][C:2]1[C:3](O)=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:3]1[C:2]([I:1])=[CH:7][N:6]=[C:5]2[CH:8]=[CH:9][S:10][C:4]=12

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 178516695HCID 178516695, 화합물

생성물 1

HCID 867174727-Chloro-6-iodothieno[3,2-b]pyridine수율 44%

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온도: 120 °C

실험 절차

A mixture of the crude 6-iodothieno[3,2-b]pyridin-7-ol (0.99 g, 3.6 mmol) in phosphoryl chloride (20 mL) was heated at 120° C. for 2 h. The reaction was cooled to room temperature, concentrated under reduced pressure. The residue was co-evaporated with toluene, then diluted with dichloromethane and neutralized carefully with sat. NaHCO3 solution. The black tar was filtered off and the filtrate was transferred to a separation funnel. The organic layer was concentrated and purified on silica gel (eluting with 0-35% EtOAc/hexanes) to give the desired product (44% in 2 steps). LCMS calculated for C7H4ClINS (M+H)+: m/z=295.9. Found: 295.8.

후처리

temperatureThe reaction was cooled to room temperature
concentrationconcentrated under reduced pressure
additiondiluted with dichloromethane and neutralized carefully with sat. NaHCO3 solution
filtrationThe black tar was filtered off
customthe filtrate was transferred to a separation funnel
concentrationThe organic layer was concentrated
custompurified on silica gel (eluting with 0-35% EtOAc/hexanes)

출처 및 근거

ORD 기록: ord-23e3db47c5dc45aaab387cd855a348cb
출처 데이터셋: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09181271B2

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