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

HRID 715235Notes

Reaction equation

HRID 715235 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.[CH3:15][C:16]1[CH:17]=[C:18]([CH:28]([NH2:30])[CH3:29])[CH:19]=[N:20][C:21]=1[O:22][CH2:23][C:24]([F:27])([F:26])[F:25]>>[Cl:13][C:12]1[C:3]2[CH2:2][N:30]([CH:28]([C:18]3[CH:19]=[N:20][C:21]([O:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[C:16]([CH3:15])[CH:17]=3)[CH3:29])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 675095881-(5-Methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate

Product 1

HCID 898749364-chloro-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 62%

Procedure

The title compound is prepared in 62% yield (135 mg, colorless oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (154 mg, 0.57 mmol, Amine-37, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-79f4405d963940f3a0193937c8a5512e
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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