3-Bromopyridine → 6-Methyl-3-(pyridin-3-ylamino)-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide

HRID 2219482Notes

Reaction equation

HRID 2219482 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]([C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[S:5][CH:6]=1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]([C:10]2[C:15]([NH:16][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:13]=[C:12]([CH3:17])[N:11]=2)=[O:9])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 86607571HCID 86607571, compound

Product 1

HCID 115371406-Methyl-3-(pyridin-3-ylamino)-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound, was prepared in accordance with the general method of example 4, step 2 using 2-amino-4-methylthiazole instead of 2-chloro-4-aminopyridine to yield 6-Methyl-2-(4-methyl-thiazol-2-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester as a light yellow solid. MS (ISP): m/e=349.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide as an off-white solid, MS (ISP): m/e=249.4 (M+H+). Palladium catalysed arylation with 3-Bromopyridine as described in example 4 step 4 yielded the final product as a yellow solid, MS (ISP): m/e=326.0 (M+H+).

Sources & evidence

ORD record
ord-14498d3bbe6942c49bb7aeabdcafed4c
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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