Dichloromethane → N-[5-(6-Chloro-5-methylsulfonyl-pyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[N:6][CH:7]=1.ClCCl.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].I[C:40]1[S:44][C:43]([NH:45][C:46](=[O:48])[CH3:47])=[N:42][C:41]=1[CH3:49].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)C>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([C:40]2[S:44][C:43]([NH:45][C:46](=[O:48])[CH3:47])=[N:42][C:41]=2[CH3:49])=[CH:3][C:4]=1[S:9]([CH3:12])(=[O:11])=[O:10]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 5-bromo-2-chloro-3-methylsulfonylpyridine (0.135 g, 0.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (24 mg, 0.03 mmol), bis(pinacolato)diboron (0.135 g, 0.53 mmol) and potassium acetate (0.147 g, 1.5 mmol) in 1,4-dioxane (4 mL) was heated at 80° C. for 18 hours. The reaction mixture was cooled and N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide (100 mg, 0.35 mmol), 2M aqueous sodium carbonate (1.25 mL, 2.5 mmol), ethanol (0.6 mL) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (12 mg, 0.015 mmol) were added. The resultant mixture was heated again at 80° C. for 8 hours. The resultant mixture was filtered through a plug of celite and purified with preparative HPLC (Method A) to give the title compound (30 mg, 17%; retention time
Workup
- temperatureThe reaction mixture was cooled
- filtrationThe resultant mixture was filtered through a plug of celite
- custompurified with preparative HPLC (Method A)
Sources & evidence
- ORD record
- ord-9120a475908a4278a393aa7264e33b75
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868188B2
Reaction notes
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