Bromine → 5-Bromo-3-(phenylthio)pyridin-2-amine

HRID 335124노트

반응식

HRID 335124 반응식
[N+:1]([C:4]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[Br:17]Br>[Zn].CC(O)=O>[Br:17][C:7]1[CH:8]=[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([NH2:1])=[N:5][CH:6]=1

참가 물질

5

반응물 2

HCID 24408BromineHCID 669950202-Nitro-3-(phenylthio)pyridine

생성물 1

HCID 459260645-Bromo-3-(phenylthio)pyridin-2-amine수율 92.21%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

mL 2-Nitro-3-(phenylthio)pyridine (16.3 g, 70.2 mmol) and AcOH (250 mL) were cooled in a water bath. Zinc (22.9 g, 351 mmol) was slowly added and stirred for 5 minutes. Filtered through celite and the cake washed with CH2Cl2. The CH2Cl2 was removed and to the solution was added bromine (3.6 mL, 70.2 mmol). After 10 minutes, the HOAc was removed and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (1.5 L SiO2 and 30% EtOAc in hexanes) to afford the title compound (18.2 g, 92.21% yield).

후처리

  1. filtrationFiltered through celite
  2. washthe cake washed with CH2Cl2
  3. customThe CH2Cl2 was removed and to the solution
  4. waitAfter 10 minutes
  5. customthe HOAc was removed
  6. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on silica gel (1.5 L SiO2 and 30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-b9963ac8602f420c9212669806f6d897
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

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