2-BROMO-5-HYDROXYMETHYLTHIAZOLE

2-Bromothiazole-5-carbaldehyde (3.00 g, 15.62 mmol) and methanol (50 mL) were combined. The mixture was cooled to 0 °C under nitrogen and sodium borohydride (0.591 g, 15.62 mmol) was added portion wise. Stirring was continued at this temperature for 2 hours. The reaction was then warmed to room temperature and stirred for two additional hours. The solvent was concentrated and saturated aqueous NHPreparation of 2p: iV-(Pyridin-2-yl)-5-((thiazol-2-ylamino)methyl)thiazol-2-ainine trihydrochloride; ethyl 2-bromothiazole-To a mixture of Under N2 protection, The compound N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-6-(4, 4, 5, 5-tetramethyl-1, 3 was added to a 250 mL two-necked flask. , 2-dioxaborolan-2-yl)quinazolin-4-amine (3.09 g, 6.24 mmol), Tetrakis(triphenylphosphine)palladium (0.36 g, 0.31 mmol), 2-bromothiazole-5-yl)methanol (1.55 g, 8.11 mmol), Barium carbonate (6.1 g, 18.7 mmol), 1, 4-Dioxane (60 mL) and distilled water (20 mL) were added by a syringe, and the mixture was slowly warmed to 100 C and stirred for 3.0 h.Concentrated, add dichloromethane (200 mL), The organic phase was washed once with distilled water (60 mL).Anhydrous sodium sulfate (7 g) was dried and concentrated to give a red brown oil.Separated by column chromatography (eluent: DCM/MeOH (v/v) = 90/1), 0.45 g of a pale yellow solid were obtained in a yield: 15%.Into a 250-mL round-bottom flask, was placed A solution of (20 g, 0.103 mol, 1 eq.), 2-methylpyridine-5-acid (18.3 g, 0.134 mol, 1.3 eq.), ATAphos*PdCl2 (3.65 g, 5.152 mmol, 0.05 eq.), Cs2CO3 (67.14 g, 0.206 mol, 2 eq.) was dissolved in THF (800 ml) and water (800 ml). The mixture was flushed with nitrogen and stirred at 80 C for 3 hours. The mixture was cooled to room temperature and diluted with EEO (300 ml). The layers were separated and the aqueous layer was extracted with EEO (3 x 100 ml) and the combined organic layers were dried over MgSO4 and evaporated after filtration. The residue was crystallized from EEO/DIPO, filtered and dried in vacuo to give a brown solid.Intermediate I-1 (0.025 g, 0.074 mmol) and A reaction vial was charged with 4-fluoro-6-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)benzo[c][1, 2, 5]oxadiazole (0.40 g, 1.50 mmol), j00392] The mixture of (2-brornothiazoi--5-yl)methanol (180 mg, 0.93 nirnol), 1- (bromomethyi)-3-trifiuoromethyl)benzene (288 mg, 1, 2 mmol) and NaOH (67 mg, 1, 67 mmol) in DMF (2 mL) was stirred at 120 C for 3h. The residue was extracted with chioroforni and iso-propanol (4:1). The organic phase was washed with brine (20 mL x 2) and dried over Na2SO4. Afler removal of the solvent, the residue was purified by silica gel (PE/EA 0-50%) to obtain MFW3-lil-1 (1 60 mg, yield 49%). LCMS (mk): 353 [M + H]j00396] The mixture of (2-bromothiazo15yl)methanol (220 mg, 1.1 mrnol), 54ertbutyF-2-(chlorornethyl)oxazole (256 mg, 1.5 mmol) and NaOH (82 rng, 2, O4mmol) in DMF (2 inL) was stirred at 120 C for 3}i. The residue was extracted with chloroform and iso-propanol (4:1). The organic phase was washed with brine (20 nt) and dried over Na2 SO4. After removal of the solvent, the residue was purified by silica gel (PE/EA = 0-50%) to obtain MFH.-3114 (170 Trig, yield 45%). LCMS (mz): 332 [M ±2-Bromo-5-(methoxymethyl)thiazole:In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of

Molecular Weight:194.05
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:192.91970
Monoisotopic Mass:192.91970
Topological Polar Surface Area:61.4
Heavy Atom Count:8
Complexity:82.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes