Ethyl 3-(bromomethyl)-2-chloroisonicotinate → 4-chloro-2-(1-(4-methyl-5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715268Notes

Reaction equation

HRID 715268 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[C:22]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=[C:19]([CH:29]([NH2:31])[CH3:30])[CH:18]=1>>[Cl:14][C:13]1[C:3]2[CH2:2][N:31]([CH:29]([C:19]3[CH:18]=[C:17]([CH3:16])[C:22]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[CH:21][N:20]=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 89874857HCID 89874857, compound

Product 1

HCID 898754334-chloro-2-(1-(4-methyl-5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 78%

Procedure

The title compound is prepared in 78% yield (320 mg, pale brown solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (300 mg, 1.1 mmol, Step-1 of Intermediate-1) and 1-(4-methyl-5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethanamine hydrochloride (330 mg, 1.1 mmol, Amine-49, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-203762ba02734a65855b47ff9d842446
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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