3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-one → ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

HRID 455617

반응식

HRID 455617 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([I:17])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.[Br-].[CH2:19]([O:21][C:22](=[O:25])[CH2:23][Zn+])[CH3:20]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:15]([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])([OH:16])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([I:17])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 2

HCID 574756483-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-oneHCID 178472538HCID 178472538, 화합물

생성물 1

HCID 67382689ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

시약·촉매·용매 2

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a suspension of tetraethoxytitanium (3.40 g, 14.93 mmol) in THF (16.58 ml) was added 3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-one (2.00 g, 4.98 mmol). The suspension was cooled to 0° C. and (2-ethoxy-2-oxoethyl)zinc(II) bromide (149 ml, 14.93 mmol) was added drop wise. The reaction mixture was allowed to warm to RT and stirred 1 h. The reaction mixture was quenched with aqueous, half-saturated NaHCO3 solution (20 mL) and stirred for 30 min. The solution was filtered through a pad of celite and the filter cake was rinsed with EtOAc. The organic layer was separated and concentrated under reduced pressure to afford ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate as a yellowish solid.

후처리

  1. temperatureto warm to RT
  2. customThe reaction mixture was quenched with aqueous, half-saturated NaHCO3 solution (20 mL)
  3. stirringstirred for 30 min
  4. filtrationThe solution was filtered through a pad of celite
  5. washthe filter cake was rinsed with EtOAc
  6. customThe organic layer was separated
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-23456014faeb4d8489221cde4e2bafc6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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