3-(Trifluoromethoxy)phenol → 6-(4-Cyanophenoxy)-5-fluoro-2-(3-trifluoromethoxyphenoxy)nicotinic acid ethyl ester

HRID 1024704Notes

Reaction equation

HRID 1024704 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[N:7][C:6]=1Cl)[CH3:2].[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[N:7][C:6]=1[O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([O:25][C:24]([F:23])([F:33])[F:34])[CH:27]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27332613-(Trifluoromethoxy)phenolHCID 866659552-Chloro-6-(4-cyanophenoxy)-5-fluoro nicotinic acid ethyl ester

Product 1

HCID 668186086-(4-Cyanophenoxy)-5-fluoro-2-(3-trifluoromethoxyphenoxy)nicotinic acid ethyl esterYield 52%

Procedure

2-chloro-6-(4-cyano phenoxy)-5-fluoro nicotinic acid ethyl ester (2.4 g, 7.49 mmol) and 3-trifluoromethoxyphenol (1.33 g, 7.49 mmol) were coupled using the procedure of Example 17(b) to afford 1.8 g of the required product. 1H NMR (DMSO-d6): δ 1.35 (3H, t), 4.4 (2H, q), 7.22 (2H, d), 7.3 (3H, d), 7.34 (1H, m), 7.54 (2H, d), 8.38 (1H, d).

Sources & evidence

ORD record
ord-b790942ebdd54f8585fb3385af00712b
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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