3-Bromopyridine → HCID 11588965, compound

HRID 2219486Notes

Reaction equation

HRID 2219486 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N: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])[S:6][CH:7]=1.Br[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>[Pd]>[F:20][C:2]([F:19])([F:1])[C:3]1[N:4]=[C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=2)=[O:10])[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 86607572HCID 86607572, compound

Product 1

HCID 11588965HCID 11588965, 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 4-Trifluoromethyl-thiazol-2-ylamine instead of 2-Chloro-4-aminopyridine to yield [6-Methyl-2-(4-trifluoromethyl-thiazol-2-ylcarbamoyl)-pyridin-3-yl]-carbamic acid tert-butyl ester as an off-white solid. MS (ISP): m/e=403.0 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (4-trifluoromethyl-thiazol-2-yl)-amide as an off-white solid, MS (ISP): m/e=303.0 (M+H+). Palladium catalysed arylation with 3-Bromopyridine as described in example 4 step 4 yielded the final product as a yellow solid, MS (ISP): m/e=380.0 (M+H+).

Sources & evidence

ORD record
ord-1c80141f96934b098524665f6ebaeabe
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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