Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate → HCID 89874608, compound

HRID 715228Notes

Reaction equation

HRID 715228 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:32])([C:28]([F:31])([F:30])[F:29])[CH2:17][O:18][C:19]1[N: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:23]=[N:24][C:19]([O:18][CH2:17][C:16]([F:32])([F:15])[C:28]([F:29])([F:30])[F:31])=[CH:20][CH:21]=3)[CH3:26])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylateHCID 87426447HCID 87426447, compound

Product 1

HCID 89874608HCID 89874608, compoundYield 56%

Procedure

The title compound is prepared in 56% yield (133 mg, colorless oil) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(6-(2,2,3,3,3-pentafluoropropoxy)pyridin-3-yl)ethanamine hydrochloride (174 mg, 0.57 mmol, Amine-20, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-fe6e4bdb8de44f3594a5bed5028c0174
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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