3-Hydroxypyridine → 4-[[2-(3-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173434Notes

Reaction equation

HRID 1173434 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.O[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>COCCOC>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([O:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:15])([F:16])[F:14])[CH:6]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 79713-HydroxypyridineHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 115746184-[[2-(3-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Synthesized as described in Example 1C from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 3-hydroxypyridine, using dry DME as reaction solvent: 1H NMR (300 MHz, CDCl3) δ 8.14 (dd, J=5.1, 1.6 Hz, 1H), 7.65 (d, J=8.9 Hz, 1H), 7.59 (ddd, J=8.5, 6.8, 1.7 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 7.04 (dd, J=8.8, 2.5 Hz, 1H), 6.91 (dd, J=6.8, 5.4 Hz, 1H), 6.70 (d, J=8.3 Hz, 1H), 4.56 (t, J=6.1 Hz, 2H), 4.11 (q, J=8.5 Hz, 2H), 3.96 (t, J=6.1 Hz, 2H).

Workup

  1. customSynthesized
  2. customas reaction solvent

Sources & evidence

ORD record
ord-d0b66a7ef8fa43ad80ff47f3f9ee0f0b
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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