Sodium hydride → 6-(2-(2,2,2-Trifluoroethoxy)ethoxy)nicotinic acid

HRID 1099457Notes

Reaction equation

HRID 1099457 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[F:13][C:14]([F:21])([F:20])[CH2:15][O:16][CH2:17][CH2:18][OH:19].[H-].[Na+]>>[F:13][C:14]([F:21])([F:20])[CH2:15][O:16][CH2:17][CH2:18][O:19][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol2×HCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 593549156-(2-(2,2,2-Trifluoroethoxy)ethoxy)nicotinic acidYield 71%

Procedure

The title compound was synthesized as described for Intermediate example I-92 in 71% yield starting from ethyl 6-chloronicotinate and 2-(2,2,2-trifluoroethoxy)ethanol. The reaction between sodium hydride and 2-(2,2,2-trifluoroethoxy)ethanol was performed at 0° C. for 3 min, then ambient temperature for 15 min and then cooled to 0° C. before ethyl 6-s chloronicotinate was added; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.71 (d, 1 H), 8.15 (dd, 1 H), 6.93 (d, 1 H), 4.42-4.52 (m, 2 H), 4.14 (q, 2 H), 3.92-3.97 (m, 2 H); MS (APPI/APCI) m/z 266[M+H+].

Workup

  1. waitambient temperature for 15 min
  2. additionwas added

Sources & evidence

ORD record
ord-78d3e6643d3b49c597be5187032d760a
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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