3-Bromopyridine → HCID 11522606, compound

HRID 2219473Notes

Reaction equation

HRID 2219473 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 86607568HCID 86607568, compound

Product 1

HCID 11522606HCID 11522606, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was prepared from 3-tert-Butoxy-carbonylamino-6-methyl-pyridine-2-carboxylic acid methyl ester in accordance with the general method of example 4; step 2 using 2-methyl-4-aminopyridine (CAS: [18437-58-6]) instead of 2-chloro-4-aminopyridine to yield [2-(2-Methyl-pyridin-4-ylcarbamoyl)-6-methyl-pyridin-3-yl]-carbamic acid tert-butyl ester, MS (ISP): m/e=343.1 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-methyl-pyridin-4-yl)-amide, MS (ISP): m/e=243.4 (M+H+). Palladium catalysed arylation with 3-Bromopyridine as described in example 4 step 4 yielded the final product as a light yellow solid, MS (ISP): m/e=320.0 (M+H+).

Sources & evidence

ORD record
ord-5cb97f18334e48a5a8e9eb96eec90713
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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