Triethylamine → Tert-butyl [1-(4-fluorophenyl)-2-oxo-2-quinolin-8-ylethyl]carbamate

HRID 1170385Notes

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[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][C:42]=2[CH:44]=[O:45])[CH:37]=[CH:36][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:44](=[O:45])[C:42]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:43]=2[N:34]=[CH:35][CH:36]=[CH:37]3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

1.9 g (5.1 mmol) of tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamate, 255 mg (1.0 mmol) of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide, 10.5 ml (76 mmol) of triethylamine and 0.72 g (4.55 mmol) of 8-quinolinecarbaldehyde were mixed in 44 ml of methylene chloride at room temperature and then heated at 35° C. for 3 h. After reaction of the aldehyde was complete, 25 ml of saturated ammonium chloride solution were added, and the reaction mixture was stirred for 15 minutes. After removal of the aqueous phase, the organic phase was washed with 0.5 M sodium hydroxide solution and saturated sodium chloride solution, and 1.7 g of tert-butyl [1-(4-fluorophenyl)-2-oxo-2-quinolin-8-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-97e4b8d38f244004b385b027d252b63b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825264B2

Reaction notes

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