Nitrogen → HCID 58456365, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:8]=1)[NH2:5].Br[C:19]1[S:23][CH:22]=[N:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].N#N>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:19]2[S:23][CH:22]=[N:21][CH:20]=2)[CH:8]=1)[NH2:5]Participants
Conditions
- Temperature
- 100 °C
Procedure
3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (20.98 g, 90 mmol), 5-bromothiazole (8.85 mL, 99 mmol), and sodium carbonate (90 mL, 180 mmol) were combined in a flask. 2-Methyl-THF (326 mL) was added and the flask was degassed with N2 for 1.5 h before 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3.67 g, 4.50 mmol) was added. The reaction was heated to 100° C. overnight and was then cooled to room temperature. The reaction mixture was filtered though a pad of Celite, washing with ethyl acetate. The layers were separated and the aqueous layer was back-extracted with ethyl acetate, dried over Na2SO4, and concentrated. The residue was purified by chromatography (0-40% ethyl acetate in hexanes). 3-Methyl-5-(1,3-thiazol-5-yl)aniline was isolated as a yellowish brown solid (15.33 g, 81 mmol, 90%). MS ESI: [M+H]+ m/z 191.1. 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 1H), 8.02 (s, 1H), 6.80 (s, 1H), 6.71 (s, 1H), 6.50 (s, 1H), 3.71 (s, 2H), 1.79 (s, 3H).
Workup
- additionwas added
- temperaturewas then cooled to room temperature
- filtrationThe reaction mixture was filtered though a pad of Celite
- washwashing with ethyl acetate
- customThe layers were separated
- extractionthe aqueous layer was back-extracted with ethyl acetate
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by chromatography (0-40% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-7b8d34549b2b44bcb5ce3cb6d6df8ee6
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
Loading…