(5-Methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine hydrochloride → 4-chloro-3-methyl-2-((5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715213Notes

Reaction equation

HRID 715213 reaction equation
Br[CH:2]([C:4]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)[CH3:3].Cl.[CH3:16][C:17]1[CH:18]=[C:19]([CH2:29][NH2:30])[CH:20]=[N:21][C:22]=1[O:23][CH2:24][C:25]([F:28])([F:27])[F:26]>>[Cl:14][C:13]1[C:4]2[CH:2]([CH3:3])[N:30]([CH2:29][C:19]3[CH:20]=[N:21][C:22]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[C:17]([CH3:16])[CH:18]=3)[C:6](=[O:8])[C:5]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 67509326(5-Methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine hydrochlorideHCID 89875505Methyl 3-(1-bromoethyl)-2-chloroisonicotinate

Product 1

HCID 898752184-chloro-3-methyl-2-((5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 20%

Procedure

The title compound is prepared in 20% yield (41 mg, pale brown oil) from methyl 3-(1-bromoethyl)-2-chloroisonicotinate (175 mg, 0.53 mmol, Step-1, racemate) and (5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine hydrochloride (146 mg, 0.53 mmol, Amine-3) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-042405d5ee0c4dc985092752029fbd32
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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