1-(6-(3,3,3-Trifluoropropoxy)pyridin-3-yl)ethanamine hydrochloride → 4-chloro-2-(1-(6-(3,3,3-trifluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715223Notes

Reaction equation

HRID 715223 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:30])([F:29])[CH2:17][CH2:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1>>[Cl:13][C:12]1[C:3]2[CH2:2][N:28]([CH:26]([C:23]3[CH:24]=[N:25][C:20]([O:19][CH2:18][CH2:17][C:16]([F:30])([F:15])[F:29])=[CH:21][CH:22]=3)[CH3:27])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 675093381-(6-(3,3,3-Trifluoropropoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate

Product 1

HCID 898750314-chloro-2-(1-(6-(3,3,3-trifluoropropoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 47%

Procedure

The title compound is prepared in 47% yield (102 mg, colorless oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(6-(3,3,3-trifluoropropoxy)pyridin-3-yl)ethanamine hydrochloride (154 mg, 0.57 mmol, Amine-15, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-133c61a8cfef482b927787a9a1638edb
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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