Triethylamine → Tert-butyl [1-(4-fluorophenyl)-2-oxo-2-pyridin-3-ylethyl]carbamate

HRID 1170387Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]=[O:41])[CH:35]=1.[Cl-].[NH4+]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[C:40](=[O:41])[C:36]2[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

10.0 g (26.4 mmol) of tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamate, 665 mg (2.6 mmol) of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide, 55 ml (395 mmol) of triethylamine and 5.6 g (26.4 mmol) of 3-pyridinecarboxaldehyde were mixed in 230 ml of methylene chloride at room temperature and then heated at 35° C. for 3 h. After reaction of the aldehyde was complete, 100 ml of saturated ammonium chloride solution were added, and the reaction mixture was stirred for 10 minutes. After removal of the aqueous phase, the organic phase was washed with 0.5 M sodium hydroxide solution and saturated sodium chloride solution. 9.7 g of tert-butyl [1-(4-fluorophenyl)-2-oxo-2-pyridin-3-ylethyl]carbamate were obtained and were reacted further without purification.

Workup

customAfter removal of the aqueous phase
washthe organic phase was washed with 0.5 M sodium hydroxide solution and saturated sodium chloride solution

Sources & evidence

ORD record: ord-3f4de9a937b84a70b57bcd3fb64327de
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825264B2

Reaction notes

Loading…