Ethyl 3-(bromomethyl)-2-chloroisonicotinate → HCID 89875244, compound

HRID 715331Notes

Reaction equation

HRID 715331 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][C:17]([F:31])([CH3:30])[CH2:18][O:19][C:20]1[CH: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]=[CH:25][C:20]([O:19][CH2:18][C:17]([F:16])([F:31])[CH3:30])=[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 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateHCID 89874989HCID 89874989, compound

Product 1

HCID 89875244HCID 89875244, compoundYield 76%

Procedure

The title compound is prepared in 76% yield (437 mg, yellow oil) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (419 mg, 1.51 mmol, Step-1 of Intermediate-1) and 1-(4-(2,2-difluoropropoxy)-3-methylphenyl)ethanamine hydrochloride (400 mg, 1.51 mmol, Amine-81, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-8d3300b2d1f64661ab594d03e842f652
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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