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

HRID 2043349

Reaction equation

HRID 2043349 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

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]+).

Workup

  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

Sources & evidence

ORD record
ord-d8f9716ec6ae47d4b562a9d806cb07a0
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Linked notes

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