1-Bromo-3,5-difluorobenzene → HCID 11574584, compound

HRID 2219533Notes

Reaction equation

HRID 2219533 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]([CH3:20])[N:14]=2)=[O:12])=[N:6]1.Br[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=1>[Pd]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:18]([NH:19][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=3)=[CH:17][CH:16]=[C:15]([CH3:20])[N:14]=2)=[O:12])=[N:6]1

Participants

4

Reactant 2

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 86607587HCID 86607587, compound

Product 1

HCID 11574584HCID 11574584, 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 1-(2-Methoxy-ethyl)-1H-pyrazol-3-yl amine instead of 2-chloro-4-aminopyridine to yield {2-[1-(2-Methoxy-ethyl)-1H-pyrazol-3-ylcarbamoyl]-6-methyl-pyridin-3-yl}-carbamic acid tert-butyl ester as a yellow oil, MS (ISP): m/e=376.5 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid [1-(2-methoxy-ethyl)-1H-pyrazol-3-yl]-amide as a yellow oil, MS (ISP): m/e=276.3 (M+H+). Palladium catalysed arylation in accordance with the general method described in example 20 using 1-Bromo-3,5-difluorobenzene instead of 3-bromopyridine yielded the final compound as a light brown solid, MS (ISP): m/e=388.4 (M+H+).

Sources & evidence

ORD record
ord-9d07c3e13ecf4c28a4aa5f30fe5822e6
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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