Triethylamine → Phenyl (6-((2-methylpyridin-3-yl)oxy)pyridin-3-yl)carbamate

HRID 840549Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[C:10]([CH3:15])=[N:11][CH:12]=[CH:13][CH:14]=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]>C(Cl)Cl>[CH3:15][C:10]1[C:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:24](=[O:25])[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:7][N:6]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: -20 °C

Procedure

5-Amino-2-(2-methylpyridin-3-yloxy)pyridine (D9, 60.3 g, 0.3 mole) in dry CH2Cl2 (2.5L) was cooled to −20° C. under argon. Triethylamine (46 ml, 0.33 mole) was added, followed dropwise by phenyl chloroformate (41 ml, 0.33 mole) and the mixture was stirred at −20° C. for 1 hour. After warming to ambient temperature, the mixture was washed with dil. aq. NaHCO3, dried (Na2SO4) and evaporated in vacuo. The residue was recrystallised from ethyl acetate/60-80° petroleum ether to afford the title compound (53.7 g, 56%) as a pink solid.

Workup

temperatureAfter warming to ambient temperature
washthe mixture was washed with dil. aq. NaHCO3
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was recrystallised from ethyl acetate/60-80° petroleum ether

Sources & evidence

ORD record: ord-d221860adb6144c5ae9d7bee5a9e6bf9
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369060B1

Reaction notes

Loading…