3-Bromopyridine → HCID 11602237, compound

HRID 2219476Notes

Reaction equation

HRID 2219476 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])=[N:6][CH:7]=1.Br[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([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])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 86607569HCID 86607569, compound

Product 1

HCID 11602237HCID 11602237, 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 2-amino-5-fluoropyridine instead of 2-chloro-4-aminopyridine to yield [2-(5-Fluoro-pyridin-2-ylcarbamoyl)-6-methyl-pyridin-3-yl]-carbamic acid tert-butyl ester as a white solid. MS (ISP): m/e=347.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (5-fluoro-pyridin-2-yl)-amide as a light yellow solid, MS (ISP): m/e=247.3 (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=324.3 (M+H+).

Sources & evidence

ORD record
ord-07d3c75897cf4a48b99bc1161a4dac79
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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