1-(4-(2,2,2-Trifluoroethoxy)phenyl)ethanamine hydrochloride → 4-chloro-2-(1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715218Notes

Reaction equation

HRID 715218 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.[F:15][C:16]([F:29])([F:28])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1>>[Cl:13][C:12]1[C:3]2[CH2:2][N:27]([CH:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:16]([F:15])([F:28])[F:29])=[CH:24][CH:23]=3)[CH3:26])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 675101261-(4-(2,2,2-Trifluoroethoxy)phenyl)ethanamine hydrochlorideHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate

Product 1

HCID 898743354-chloro-2-(1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 62%

Procedure

The title compound is prepared in 62% yield (131 mg, colorless amorphous solid) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(4-(2,2,2-trifluoroethoxy)phenyl)ethanamine hydrochloride (124 mg, 0.57 mmol, Amine-10, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-d4b0011b2d95442aa04ec53478598c52
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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