2-Bromo-4,5-dimethyl-1,3-thiazole

Preparation of 4, 5-dimethylthiazole-2-thiol; Step 1 : Bromine (6.8 mL, 132 mmol) was added to a solution of 4, 5- dimethylthiazole 1 (4.7 mL, 44 mmol) at OStep 1 : Bromine (6.8 mL, 132 mmol) was added to a solution of 4, 5- dimethylthiazole 1 (4.7 mL, 44 mmol) at 0°C, dropwise and stirred at room temperature overnight. The reaction was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography to afford 3.9 g clear oil, yield 47percent.Preparation of 4, 5-dimethylthiazole-2-thiol; Step 1 : Bromine (6.8 mL, 132 mmol) was added to a solution of 4, 5- dimethylthiazole 1 (4.7 mL, 44 mmol) at O0C, dropwise and stirred at rt overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography to afford 3.9 g clear oil, yield 47%.Step 1 : Bromine (6.8 mL, 132 mmol) was added to a solution of 4, 5- dimethylthiazole 1 (4.7 mL, 44 mmol) at 0C, dropwise and stirred at room temperature overnight. The reaction was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography to afford 3.9 g clear oil, yield 47%.A solution of ethyl 3-(3-amino-4-(diisobutylamino)phenyl)butanoate (0.100 g, 0.30 mmol), To a microwave tube equipped with a stifling bar, (R)-4-((R)-1-((1-cyclopropyl-5-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (120 mg, 0.292 mmol), A solution of 4, 5-dimethylthiazol-2-amine hydroboromide (4.94 g, 30 mmol) and isoamyl nitrite (4.42 ml, 33 mmol) in CH3CN (125 ml) was treated with CuBr (6.5 g, 45 mmol), added portion-wise, and the reaction was stirred at RT for 4 hours. Silica gel (18 g) was added, the volatiles were removed under reduced pressure, and the crude residue was purified by flash column chromatography hexane/AcOEt 98:2 to 7:3. The brown oil obtained was triturated with pentane to give 1 g of pure crystalline product. ESIMS (m/z) 192.0, 194.2 (MH+).

Molecular Weight:192.08
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Exact Mass:190.94043
Monoisotopic Mass:190.94043
Topological Polar Surface Area:41.1
Heavy Atom Count:8
Complexity:88.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes