Triethylamine → Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamate

HRID 427723Notes

Reaction equation

HRID 427723 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>ClCCl>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:24](=[O:25])[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 154477886-[(Pyridin-2-yl)methoxy]pyridin-3-amine

Product 1

HCID 11141770Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-(pyridin-2-ylmethyloxy)pyridine (D2, 1.36 g, 0.0068 mole) in dichloromethane (50 ml) was cooled to 0° C. under argon. Triethylamine (1.04 ml, 0.0075 mole) was added, followed dropwise by phenyl chloroformate (0.94 ml, 0.0075 mole) and the mixture was stirred at room temperature for 4 hours, washed with water, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate to leave the title compound (1.9 g, 87%) as a solid.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-01e1d3770fab4b048f1fbfcc843f9d1c
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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