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

HRID 2043349

反応式

HRID 2043349 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-d8f9716ec6ae47d4b562a9d806cb07a0
出典データセット
uspto-grants-2013_11
特許番号
US08586617B2

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