1-(5-Chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride → 2-bromo-N-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-6-methylisonicotinamide

HRID 623639Notes

Reaction equation

HRID 623639 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:15]([NH2:17])[CH3:16])[CH:6]=[N:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:22](O)=[O:23]>>[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:22]([NH:17][CH:15]([C:5]1[CH:6]=[N:7][C:8]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])=[C:3]([Cl:2])[CH:4]=1)[CH3:16])=[O:23]

Participants

3

Reactant 2

HCID 675090891-(5-Chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 722118522-Bromo-6-methylisonicotinic acid

Product 1

HCID 874267952-bromo-N-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-6-methylisonicotinamideYield 83%

Procedure

The title compound is prepared in 83% yield (387 mg, a yellow solid) from (+)-1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (300 mg, 1.0 mmol, Amine-5, single enantiomer) and 2-bromo-6-methylisonicotinic acid (223 mg, 1.0 mmol) by the similar manner in Step-1 of Example 8.

Sources & evidence

ORD record
ord-5c0d7103deee44fa8327e5a5e810d39e
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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