Potassium Phosphate, Tribasic → 2-Methoxy-3-(2-methylthiazol-4-yl)aniline
Reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH3:8][O:9][C:10]1[C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH3:8][O:9][C:10]1[C:16]([C:2]2[N:3]=[C:4]([CH3:7])[S:5][CH:6]=2)=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A stirred mixture of 4-bromo-2-methylthiazole (128 mg, 0.719 mmol), 2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (197 mg, 0.791 mmol) and 1,1′-bis(di-tert-Butylphosphino)ferrocene palladium dichloride (14.06 mg, 0.022 mmol) in dioxane (4 mL) was degassed by bubbling nitrogen through the mixture for 5 minutes. To this was added aqueous potassium phosphate (K3PO4, 2M, 1.078 mL, 2.157 mmol) and the reaction mixture was heated to 100° C. for one hour. The reaction mixture was cooled to room temperature, then diluted with ethyl acetate (75 mL). This solution was then dried over sodium sulfate, filtered, concentrated and purified by flash chromatography, eluting with 0-100% EtOAc in hexanes. Afforded 2-methoxy-3-(2-methylthiazol-4-yl)aniline (122 mg, 0.543 mmol, 75% yield) as a yellow oil. LC retention time 0.60 [J]. m/z: 221 (MH+).
Workup
- customwas degassed
- customby bubbling nitrogen through the mixture for 5 minutes
- temperatureThe reaction mixture was cooled to room temperature
- dry with materialThis solution was then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography
- washeluting with 0-100% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-bf4c3618a45949c283206805c93a3de5
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315494B2
Reaction notes
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