Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate → 4-chloro-2-(1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715224Notes

Reaction equation

HRID 715224 reaction equation
Br[CH2:2][C:3]1[C:12]([Cl:13])=[N:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.Cl.[Cl:15][C:16]1[CH:17]=[C:18]([CH:27]([NH2:29])[CH3:28])[CH:19]=[N:20][C:21]=1[O:22][CH2:23][CH:24]([F:26])[F:25]>>[Cl:13][C:12]1[C:3]2[CH2:2][N:29]([CH:27]([C:18]3[CH:19]=[N:20][C:21]([O:22][CH2:23][CH:24]([F:25])[F:26])=[C:16]([Cl:15])[CH:17]=3)[CH3:28])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylateHCID 874267141-(5-Chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethanamine hydrochloride

Product 1

HCID 898742894-chloro-2-(1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 71%

Procedure

The title compound is prepared in 71% yield (157 mg, colorless oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (155 mg, 0.57 mmol, Amine-16, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-2b30ba7e68b54b5d999c8c6875788771
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…