5-Bromo-6-chloropyridine-3-carboxylic acid → 5-bromo-6-chloro-N-(4-(perfluoroethoxy)phenyl)nicotinamide

HRID 73778Notes

Reaction equation

HRID 73778 reaction equation
[Br: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:26])([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[C:14]([F:17])([F:16])[F:15]>>[Br:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:13]([F:12])([F:26])[C:14]([F:15])([F:16])[F:17])=[CH:25][CH:24]=1)=[O:9]

Participants

3

Reactant 2

HCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 123287194-(Pentafluoroethoxy)aniline

Product 1

HCID 867026205-bromo-6-chloro-N-(4-(perfluoroethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 9.3 using 5-bromo-6-chloro-nicotinic acid and 4-(perfluoroethoxy)aniline to afford an off-white crystalline solid. HPLC (Condition 4) tR=6.73 min, UPLC-MS (Condition 3) tR=1.30 min, m/z=443.1 [M−H]−.

Workup

  1. customto afford an off-white crystalline solid

Sources & evidence

ORD record
ord-9cd77a866ae34b0c9f90ca13a7d7513f
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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