Acetone → 5-bromo-2-chloro-N-(propan-2-yl)pyridin-3-amine

HRID 2077532노트

반응식

HRID 2077532 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][C:11]([CH3:13])=O.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OC(C)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH:11]([CH3:13])[CH3:10])[C:5]([Cl:8])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 218583543-Amino-5-bromo-2-chloropyridine

생성물 1

HCID 575849795-bromo-2-chloro-N-(propan-2-yl)pyridin-3-amine수율 102.6%

시약·촉매·용매 1

HCID 7915Isopropyl Acetate용매

실험 절차

5-bromo-2-chloropyridin-3-amine (1.889 g, 9.1 mmol) was dissolved in isopropyl acetate (20 ml) and acetone (0.81 ml, 11 mmol), trifluoroacetic acid (1.40 ml, 18 mmol), and sodium triacetoxyborohydride (2.34 g, 11 mmol) were added. The reaction was stirred under nitrogen at room temperature for almost 4.5 hours and then quenched with 10% sodium hydroxide in water (˜20 ml) to raise the pH to about 9. The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum to afford 5-bromo-2-chloro-N-isopropylpyridin-3-amine (2.33 g, 89% purity, 100% yield). MS (ESI pos. ion) m/z: 249 (MH+, 79Br), 251 (MH+, 81Br). Calculated exact mass for C8H10BrClN2 248 (79Br), 250 (81Br).

후처리

  1. customquenched with 10% sodium hydroxide in water (˜20 ml)
  2. temperatureto raise the pH to about 9
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-a53b221b2cf048c497be4529d728db6e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928140B2

반응 노트

불러오는 중…