Pyridine → HCID 20587814, compound

HRID 496285Notes

Reaction equation

HRID 496285 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([O:21][C:22](=[O:23])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 153482-Amino-5-methylpyridineHCID 15891Phenyl chloroformate

Product 1

HCID 20587814HCID 20587814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of 5-methyl-pyridin-2-ylamine (1.0 g, 9.25 mmol) and pyridine (20 ml) in dry CH2Cl2 add phenylchloroformate (2.2 g, 13.9 mmol) and stir for 24 hours at room temperature. Add water and a solution of 1:1 EtOAc/hexanes and separate the organic layer. Wash the organic layer with 1N HCl three times and with brine once. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo. Purify by flash column chromatography (0-10% EtOAc/CH2Cl2) to obtain (5-methyl-pyridin-2-yl)-carbamic acid phenyl ester. Mass spec.: M+1=229 (AP+). B. 1′-(5-methyl-pyridin-2-yl-carbamoyl)-spiroisobenzofuran-1,4′-piperidine

Workup

  1. customAdd water and a solution of 1:1 EtOAc/hexanes and separate the organic layer
  2. washWash the organic layer with 1N HCl three times
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customPurify by flash column chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-74e6540b44844995a650049c8dd17654
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

Loading…