5,6-Dichloronicotinic acid → 5,6-dichloro-N-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide

HRID 629079Notes

Reaction equation

HRID 629079 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[F:12][C:13]([F:23])([F:22])[O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([O:14][C:13]([F:12])([F:22])[F:23])=[CH:16][CH:17]=1)=[O:9]

Participants

3

Reactant 2

HCID 2479875,6-Dichloronicotinic acidHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 81946485,6-dichloro-N-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 30.1 using 5,6-dichloronicotinic acid and 4-(trifluoromethoxy)aniline to afford an off-white solid. UPLC-MS (Condition 1) tR=3.05 min, m/z=350.9/352.9 [M+H]+, m/z=348.9/351.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.40 (d, J=8.6 Hz, 2H) 7.86 (d, J=9.3 Hz, 2H) 8.63 (d, J=2.0 Hz, 1H) 8.90 (d, J=2.2 Hz, 1H) 10.70 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-890949c94bcf4dffaedbad4063e8e6ed
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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