Azidotrimethylsilane → (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol

HRID 455592노트

반응식

HRID 455592 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:17][O:16]3)[C:14]3[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[N:20]([Si](C)(C)C)=[N+:21]=[N-:22]>CN(C=O)C.CCOC(C)=O.O>[N:20]([C:15]1([CH2:17][OH:16])[C:14]2[CH:13]=[C:12]([Cl:18])[N:11]=[C:10]([F:19])[C:9]=2[O:8][C:5]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N+:21]=[N-:22]

참가 물질

6

반응물 2

HCID 78378Azidotrimethylsilane2회HCID 866583687-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2'-oxirane]

생성물 1

HCID 86658369(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol수율 99%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,2′-oxirane] (23.5 g, 68.6 mmol) in DMF (600 mL) was added azidotrimethylsilane (54.6 mL, 412 mmol). The reaction mixture was stirred at RT for 6 hours. Additional azidotrimethylsilane (54.6 mL, 412 mmol) was added and the reaction was stirred at RT for 18 hours. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, washed sequentially with a saturated aqueous LiCl solution and brine before drying over sodium sulfate. The solution was concentrated under reduced pressure to afford (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (26.12 g, 67.7 mmol, 99% yield).

후처리

  1. stirringthe reaction was stirred at RT for 18 hours
  2. customThe organic layer was separated
  3. washwashed sequentially with a saturated aqueous LiCl solution and brine
  4. dry with materialbefore drying over sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fe65a7638c71404ebbcdab8340b98396
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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