Ethyl 3-(bromomethyl)-2-chloroisonicotinate → HCID 89875482, compound

HRID 715283Notes

Reaction equation

HRID 715283 reaction equation
Br[CH2:2][C:3]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7]CC)=O.Cl.[CH3:16][C:17]1[CH:18]=[C:19]([CH:29]([NH2:31])[CH3:30])[CH:20]=[N:21][C:22]=1[CH2:23][CH2:24][C:25]([F:28])([F:27])[F:26]>>[Cl:14][C:13]1[C:3]2[CH2:2][N:31]([CH:29]([C:19]3[CH:20]=[N:21][C:22]([CH2:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[C:17]([CH3:16])[CH:18]=3)[CH3:30])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateHCID 89874691HCID 89874691, compound

Product 1

HCID 89875482HCID 89875482, compoundYield 89%

Procedure

The title compound is prepared in 89% yield (560 mg, white solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (460 mg, 1.6 mmol, Step-1 of Intermediate-1) and 1-(5-methyl-6-(3,3,3-trifluoropropyl)pyridin-3-yl)ethanamine hydrochloride (440 mg, 1.6 mmol, Amine-64, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-002f672a9abb46a19518f35ca80b2c71
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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