Bromine → Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamate

HRID 2366785노트

반응식

HRID 2366785 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([F:23])=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=2)=[N:6][CH:7]=1.[S-:24][C:25]#[N:26].[K+].BrBr>C(O)(=O)C>[C:18]([O:17][C:16](=[O:22])[NH:15][C:13]1[CH:14]=[C:9]([O:8][C:5]2[N:6]=[C:7]3[S:24][C:25]([NH2:26])=[N:1][C:2]3=[CH:3][CH:4]=2)[CH:10]=[CH:11][C:12]=1[F:23])([CH3:19])([CH3:20])[CH3:21]

참가 물질

5

반응물 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 86657970Tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamate

생성물 1

HCID 86657972Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamate수율 90.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamate (3.00 g, 9.4 mmol) and potassium thiocyanate (3.93 g, 40 mmol) in acetic acid (40 mL) was added dropwise bromine (2.40 g, 15 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. The yellow insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue, and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (3.20 g, 90%) as a pale-yellow powder.

후처리

  1. temperaturecooling
  2. filtrationThe yellow insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionSaturated aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-e6f5acc7e9f84439b40282bff777c952
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697874B2

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