Ethyl 3-(bromomethyl)-2-chloroisonicotinate → HCID 89874891, compound

HRID 715280Notes

Reaction equation

HRID 715280 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.[Cl:16][C:17]1[CH:18]=[C:19]([CH:30]([NH2:32])[CH3:31])[CH:20]=[N:21][C:22]=1[O:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27]>>[Cl:14][C:13]1[C:3]2[CH2:2][N:32]([CH:30]([C:19]3[CH:20]=[N:21][C:22]([O:23][CH2:24][CH2:25][C:26]([F:28])([F:29])[F:27])=[C:17]([Cl:16])[CH:18]=3)[CH3:31])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateHCID 89874901HCID 89874901, compound

Product 1

HCID 89874891HCID 89874891, compoundYield 60%

Procedure

The title compound is prepared in 60% yield (450 mg, pale brown solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (500 mg, 1.8 mmol, Step-1 of Intermediate-1) and 1-(5-chloro-6-(3,3,3-trifluoropropoxy)pyridin-3-yl)ethanamine hydrochloride (480 mg, 1.8 mmol, Amine-61, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-5d307384dba1481dadf28284e201efc4
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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