4-Nitrophenyl chloroformate → 3-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl ester

HRID 1469355

Reaction equation

HRID 1469355 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C([N:27]1[CH2:30][CH:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([I:38])=[CH:34][N:33]=2)[CH2:28]1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:27]2[CH2:28][CH:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([I:38])=[CH:34][N:33]=3)[CH2:30]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 580731012-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine

Product 1

HCID 580730963-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-nitrophenyl chloroformate (692 mg g, 3.44 mmol) was added to a stirred solution of 2-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine (1.01 g, 2.29 mol) in dichloromethane (40 mL) at ambient temperature. The resulting solution was stirred at ambient temperature for 18 hr. The solvent was removed in vacuo and the product purified by flash chromatography on silica gel (25 g) eluting with dichloromethane to afford the title compound as a colourless solid (474 mg, 47%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product purified by flash chromatography on silica gel (25 g)
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-2dd9821c3568483fa3d3f81ac3c06d1c
Source dataset
uspto-grants-2015_04
Patent number
US09006269B2

Linked notes

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