3-Bromopyridine → HCID 11573128, compound

HRID 2219484Notes

Reaction equation

HRID 2219484 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][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])=[N:3]1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][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])=[N:3]1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 69352802HCID 69352802, compound

Product 1

HCID 11573128HCID 11573128, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound, was prepared in accordance with the general method of example 4, step 2 using 1-Methyl-1H-pyrazol-3-ylamine instead of 2-chloro-4-aminopyridine to yield [6-Methyl-2-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester as an off-white solid. MS (ISP): m/e=332.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide as an off-white solid, MS (ISP): m/e=232.3 (M+H+). Palladium catalysed arylation with 3-Bromopyridine as described in example 4 step 4 yielded the final product as a light brown solid, MS (ISP): m/e=309.1 (M+H+).

Sources & evidence

ORD record
ord-61d83f2af95e4a8e95ec86e21c9ac76d
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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