Cesium carbonate → 2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2Br)=[O:10])=[N:6][CH:7]=1.[CH3:18][C:19]1[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][N:20]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2[NH:25][C:24]2[C:19]([CH3:18])=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:10])=[N:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-bromo-2-methyl-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide (0.24 g, 0.76 mmol) and 2-methyl-pyridin-3-ylamine (0.099 g, 0.92 mmol) in dry dioxane (12 ml) was degassed by sonication and argon bubbling. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.149 g, 0.26 mmol) and palladium dibenzylideneacetone chloroform complex (0.081 g, 0.08 mmol) were added and the mixture was stirred until dissolution was complete. Finally, the mixture was treated with cesium carbonate (0.495 g, 1.52 mmol) and irradiated in a microwave oven at 100° C. for 10 min, 130° C. for 10 min and 150° C. for 10 min. The solvent was removed under vacuum and the residue purified by flash chromatography (heptane, ethyl acetate) to yield the title compound (0.178 g, 68%) as a light brown solid, MS (ISP): m/e=344.0 (M+H+).
Workup
- customirradiated in a microwave oven at 100° C. for 10 min, 130° C. for 10 min and 150° C. for 10 min
- customThe solvent was removed under vacuum
- customthe residue purified by flash chromatography (heptane, ethyl acetate)
Sources & evidence
- ORD record
- ord-8a95f10442db482b93b821c1ecd3afe6
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678815B2
Reaction notes
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