Sodium Carbonate → (2,6-difluorophenyl)-N-[5-(5-chlorobenzoxazol-6-yl)(1,3-thiazol-2-yl)]carboxamide
Reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[O:9])=[N:4][CH:3]=1.[Cl:18][C:19]1[C:20](B2OC(C)(C)C(C)(C)O2)=[CH:21][C:22]2S[CH:25]=[N:24][C:23]=2[CH:27]=1.C(=O)([O-])[O-:38].[Na+].[Na+].CC(=O)OCC.[Cl-].[Na+].O>COCCOC.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[C:8]([NH:7][C:5]1[S:6][C:2]([C:20]2[C:19]([Cl:18])=[CH:27][C:23]3[N:24]=[CH:25][O:38][C:22]=3[CH:21]=2)=[CH:3][N:4]=1)=[O:9]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 110 °C
Procedure
A mixture of N-(5-bromo(1,3-thiazol-2-yl))(2,6-difluorophenyl)carboxamide (38 mg, 0.12 mmol), 5-chloro-6-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzothiazole (20) (34 mg, 0.12 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 14 mg) and sodium carbonate (38 mg) in 1.0 ml DME, 0.5 ml EtOH and 0.25 ml water was heated under Ar in microwave reactor at 110° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to prep HPLC purification to give 7.1 mg (2,6-difluorophenyl)-N-[5-(5-chlorobenzoxazol-6-yl)(1,3-thiazol-2-yl)]carboxamide (51) as pale brown solid (yield: 14.5%; purity>95%). LC-MS: calcd. for C17H8ClF2N3OS2: 408 (M+1).
Workup
- concentrationphase was concentrated
- customHPLC purification
Sources & evidence
- ORD record
- ord-a6a6563491614ce6912b2808d6cdafaf
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079891B2
Reaction notes
Loading…