Phosphoric Acid → 3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-one

HRID 455550노트

반응식

HRID 455550 반응식
OP(O)(O)=O.[Br:6][C:7]1[CH:8]=[N:9][C:10]([O:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=O>O>[Br:6][C:7]1[CH:15]=[C:11]2[C:12](=[O:14])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([I:23])[CH:21]=3)[O:16][C:10]2=[N:9][CH:8]=1

참가 물질

4

반응물 2

HCID 1004Phosphoric AcidHCID 574756375-Bromo-2-(4-iodophenoxy)nicotinic acid

생성물 1

HCID 574756483-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-one수율 85.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
117.5 °C

실험 절차

A 5 L 3-neck flask equipped with an overhead stirrer, a thermometer and nitrogen inlet was charged with PPA (4 Kg, 1942 mL) (115% H3PO4) and heated to 115-120° C. 5-Bromo-2-(4-iodophenoxy)nicotinic acid (400 g, 952 mmol) was charged portion wise to the hot PPA. The viscous mixture was then allowed to stir overnight (16-18 h) at 115-120° C. The dark viscous mixture was cooled to 60-65° C. and poured slowly onto a mixture of ice (3000 g) and water (2000 mL) under mechanical stirring. The light brown slurry was allowed to stir overnight and filtered at RT. The wet cake was washed with water (2×1000 mL) followed by IPA (1500 mL) and hexane (2×1000 mL). The solid was dried to obtain 326.4 g of 3-Bromo-7-iodo-5H-chromeno[2,3-b]pyridine-5-one as a grey solid.

후처리

  1. customA 5 L 3-neck flask equipped with an overhead stirrer
  2. temperatureThe dark viscous mixture was cooled to 60-65° C.
  3. stirringto stir overnight
  4. filtrationfiltered at RT
  5. washThe wet cake was washed with water (2×1000 mL)
  6. customThe solid was dried

출처 및 근거

ORD 기록
ord-dafad0659b4240dca6fa2ce091df8046
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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