2,2,2-Trifluoroethanol → 5-Bromo-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinic acid ethyl ester

HRID 598226Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([Br:12])[C:9](=[O:13])[NH:8][C:7]=1[C:14]([F:17])([F:16])[F:15])=[O:5])[CH3:2].[CH2:18](O)[C:19]([F:22])([F:21])[F:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[C:10]([Br:12])[C:9]([O:13][CH2:18][C:19]([F:22])([F:21])[F:20])=[N:8][C:7]=1[C:14]([F:17])([F:15])[F:16])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5-Bromo-1,6-dihydro-6-oxo-2-(trifluoromethyl)-3-pyridinecarboxylic acid ethyl ester (CAS Registry No. 862111-61-3) (5.0 g, 16 mmol) was dissolved in tetrahydrofuran (80 mL). To the solution were added trifluoroethanol (1.37 mL, 19 mmol), triphenylphosphine (5.0 g, 19 mmol) and diethyl azodicarboxylate (3.7 mL, 19 mmol) at 0° C. The mixture was stirred for 30 min at 0° C. and for 6 h at room temperature. The solvent was removed in vacuo and the residue dissolved in dichloromethane and washed with water. Organic phases were pooled, dried with MgSO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel with dichloromethane:heptane 1:2 to yield the product as white solid, MS (ISP) 397 (M+H)+.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue dissolved in dichloromethane
washwashed with water
dry with materialdried with MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel with dichloromethane:heptane 1:2

Sources & evidence

ORD record: ord-a424042c83ec40a4bf7f0631cb14a61e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897621B2

Reaction notes

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