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

HRID 715221Notes

Reaction equation

HRID 715221 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.[CH3:14][O:15][C:16]1[C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=[C:18]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:17]=1>>[Cl:13][C:12]1[C:3]2[CH2:2][N:23]([CH2:22][C:21]3[C:16]([O:15][CH3:14])=[N:17][C:18]([O:24][CH2:25][C:26]([F:27])([F:28])[F:29])=[CH:19][CH:20]=3)[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 67509640(2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamineHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate

Product 1

HCID 898741214-chloro-2-((2-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 80%

Procedure

The title compound is prepared in 80% yield (177 mg, colorless oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and (2-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanamine (155 mg, 0.57 mmol, Amine-13) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-570e8d783809445f9eade547b1fabbba
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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