Acetic Acid → (3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine

HRID 2043349

반응식

HRID 2043349 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16][C:17]1[N:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][CH2:23][C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:16])[N:22]=2)[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 928923-BenzyloxyanilineHCID 516892Sodium BicarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 86620293(3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine수율 80%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a solution of 3-benzyloxyaniline (0.70 g, 3.51 mmol) in 1,2-dichloroethane (10 ml) were added 6-bromo-pyridine-2-carboxaldehyde (0.65 g, 3.51 mmol), sodium triacetoxyborohydride (1.49 g, 7.03 mmol) and acetic acid (0.80 ml, 14.1 mmol). The reaction mixture was shaken at 40° C. overnight. For work-up dichloromethane (100 ml) and 1 M sodium bicarbonate solution (40 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=3:1) to yield an orange oil (1.03 g, 80%); MS (ISP): 371.1 ([81Br M+H]+), 369.1 ([79Br M+H]+).

후처리

  1. stirringthe mixture was shaken
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-d8f9716ec6ae47d4b562a9d806cb07a0
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586617B2

연결된 노트

불러오는 중…