2-BroMo-5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Reference Example 4 2-Bromo-5-methyl-4, 5, 6, 7-tetrahydrothiazolo[5, 4-c]pyridine (1-br) (method described in International Patent Publication No. WO 2005/047296) [Referential Example 10] lithium 5-methyl-4, 5, 6, 7-tetrahydrothiazolo[5, 4-c]-pyridine-2-carboxylate: The compound (531 mg) obtained in Referential was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at -78C, and the mixture was stirred for 30 minutes with ice cooling.. After passing carbon dioxide into the reaction mixture at -78C for 10 minutes, the mixture was warmed to room temperature.. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg).1H-NMR (DMSO-d6) delta: 2.37(3H, s), 2.64-2.85(4H, m), 3.54(2H, s). (531 mg) was dissolved in anhydrous diethyl ether (20 ml), followed by the dropwise addition of n-butyl lithium (a 1.54N hexane solution, 1.63 ml) at -78C. Under ice cooling, the mixture was stirred for 30 minutes. After a CO2 gas was introduced into the reaction mixture at -78C for 10 minutes, the mixture was heated to room temperature. The reaction mixture was concentrated under reduced pressure, whereby the title compound (523 mg) was obtained.1H-NMR(DMSO-d6) delta: 2.37(3H, s), 2.64-2.85(4H, m), 3.54(2H, s).Add 245g (1.051mol) 109C3-00 to the reaction flask. Add 630g of ethanol, Stir, Heating to between 50 and 55 C; Temperature control does not exceed 65 C, A solution of 376 g (2.159 mol) of sodium dithionite and 1500 g of water was added dropwise; After the completion of the dropwise addition, the temperature is maintained at 65 to 70 C, and the reaction is about 16 to 20 hr. After the reaction is completed, the ethanol is concentrated under reduced pressure; The obtained residue is cooled to 20 to 25 C, a solution prepared by formulating 88 g (2.200 mol) of sodium hydroxide and 175 g of water to adjust the system pH=14; Extracted four times with toluene (750g × 4); The organic phase was combined, dried over anhydrous sodium sulfate, filtered, and then filtered and filtered, and the filtrate was collected, and the filtrate was concentrated to give an oily residue 109 C4-00 about 145 g (theoretical amount: 162.1 g; The residue obtained can be used in the subsequent reaction without purification). The yield was 89.5%.Add 2500g of water to the reaction flask. Add 1275g (~7.576mol) of 48% hydrobromic acid aqueous solution, Add 500g (1.510mol) 109C2-10, After stirring evenly, 17.5 g (78.35 mmol) of copper bromide was added. Temperature control does not exceed 10 C, A solution of 156 g (2.266 mol) of sodium nitrite / 750 g of water was added dropwise. After the addition is completed, The heat preservation was carried out for 3 hr between 20 and 25 C. After the reaction is completed, Temperature control does not exceed 20 C, a solution prepared by dissolving 410 g (10.25 mol) of sodium hydroxide and 820 g of water, Regulating system pH'13; Extracted three times with toluene (1500 g × 3); All the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and then filtered and evaporated. The brown oily residue 109C3-00 was obtained in an amount of about 247 g (containing about 10 to 10% of 109C4-00, theoretical amount: 352.1 g). The yield was 70.2%.

Molecular Weight:233.13
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Exact Mass:231.96698
Monoisotopic Mass:231.96698
Topological Polar Surface Area:44.4
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes