3-Bromopyridine → HCID 11530141, compound

HRID 2219479Notes

Reaction equation

HRID 2219479 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]([C:12]2[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=2)=[O:11])=[N:6][C:7]=1[CH3:8].Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]([C:12]2[C:17]([NH:18][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=2)=[O:11])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 86607570HCID 86607570, compound

Product 1

HCID 11530141HCID 11530141, 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-amino-5-fluoro-6-methylpyridine (Sanchez & al., J. Heterocycl. Chem. 24, 215(1987); CAS:[110919-71-6]) instead of 2-chloro-4-aminopyridine to yield [2-(5-Fluoro-6-methyl-pyridin-2-ylcarbamoyl)-6-methyl-pyridin-3-yl]-carbamic acid tert-butyl ester, white solid, MS (ISP): m/e=361.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (5-fluoro-6-methyl-pyridin-2-yl)-amide, white solid, MS (ISP): m/e=261.3 (M+H+). Palladium catalysed arylation with 3-Bromopyridine as described in example 4 step 4 yielded the final product as a yellow solid, (ISP): m/e=338.1 (M+H+).

Sources & evidence

ORD record
ord-87fd1719c4cc435aa5d57d0014c25fc9
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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