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

HRID 715212Notes

Reaction equation

HRID 715212 reaction equation
Br[CH2:2][C:3]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7]CC)=O.Cl.[F:16][CH:17]([F:30])[CH2:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH:26]([NH2:28])[CH3:27])=[CH:22][C:21]=1[CH3:29]>>[Cl:14][C:13]1[C:3]2[CH2:2][N:28]([CH:26]([C:23]3[CH:24]=[N:25][C:20]([O:19][CH2:18][CH:17]([F:30])[F:16])=[C:21]([CH3:29])[CH:22]=3)[CH3:27])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 874263351-(6-(2,2-Difluoroethoxy)-5-methylpyridin-3-yl)ethanamine hydrochlorideHCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinate

Product 1

HCID 898745294-chloro-2-(1-(6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 48%

Procedure

The title compound is prepared in 48% yield (178 mg, pale yellow oil) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (279 mg, 1.0 mmol, Step-1 of Intermediate-1) and 1-(6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)ethanamine hydrochloride (253 mg, 1.0 mmol, Amine-5, single enantiomer) in a similar manner to Step-2 of Intermediate-1.

Sources & evidence

ORD record
ord-9b1c4182f54c46aa9fc6b1f386261d30
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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