Ethyl 3-(bromomethyl)-2-chloroisonicotinate → HCID 89873957, compound

HRID 715264Notes

Reaction equation

HRID 715264 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.[NH2:16][CH:17]([C:19]1[CH:20]=[C:21]([CH3:31])[C:22]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[N:23][CH:24]=1)[CH3:18]>>[Cl:14][C:13]1[C:3]2[CH2:2][N:16]([CH:17]([C:19]3[CH:24]=[N:23][C:22]([NH:25][CH2:26][C:27]([F:30])([F:28])[F:29])=[C:21]([CH3:31])[CH:20]=3)[CH3:18])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateHCID 89875036HCID 89875036, compound

Product 1

HCID 89873957HCID 89873957, compoundYield 62%

Procedure

The title compound is prepared in 62% yield (220 mg, pale yellow solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (260 mg, 0.93 mmol, Step-1 of Intermediate-1) and 5-(1-aminoethyl)-3-methyl-N-(2,2,2-trifluoroethyl)pyridin-2-amine hydrochloride (250 mg, 0.93 mmol, Amine-46, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-788e284e23034e59a1cbd4ceae5d14b8
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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