Ethyl 3-(bromomethyl)-2-chloroisonicotinate → HCID 89874662, compound

HRID 715260Notes

Reaction equation

HRID 715260 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]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[N:29]=[CH:28][C:27]([CH:30]([NH2:32])[CH3:31])=[CH:26][C:25]=2[CH3:33])=[CH:19][CH:18]=1>>[Cl:14][C:13]1[C:3]2[CH2:2][N:32]([CH:30]([C:27]3[CH:28]=[N:29][C:24]([S:23][C:20]4[CH:19]=[CH:18][C:17]([F:16])=[CH:22][CH:21]=4)=[C:25]([CH3:33])[CH:26]=3)[CH3:31])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinateHCID 89874863HCID 89874863, compound

Product 1

HCID 89874662HCID 89874662, compoundYield 48%

Procedure

The title compound is prepared in 48% yield (290 mg, off white solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (400 mg, 1.4 mmol, Step-1 of Intermediate-1) and 1-(6-((4-fluorophenyl)thio)-5-methylpyridin-3-yl)ethanamine hydrochloride (410 mg, 1.6 mmol, Amine-42, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-a100b1781f554a11bbb3098b83d27a5c
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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