6-BroMopyrazolo[1,5-a]pyridine

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40percent aqueous HUnder N2 atmosphere, to a mixture of Under the protection of N2, To To a solution of 6-bromopyrazolo[l, 5-a]pyridine (CAS 1264193-11-4; 650 mg, 3.3 mmol, 1 eq.) in ACN under N2 atmosphere is introduced Y-Iodosuccinimide (780 mg, 3.46 mmol, 1.05 eq.). The resulting solution is stirred at RT overnight. [0439] The reaction mixture is filtered and the solid is washed with few milliliters of ACN to afford 6- bromo-3-iodo-pyrazolo[l, 5-a]pyridine, which is used as such in the next step.230 Compound 230 was prepared according to the following procedures: To a solution of 6- bromopyrazolo[l, 5-a]pyridine (500.0 mg, 2.54 mmol, 1.0 eq) and l-methyl-4-(4- piperidyl)piperazine (697.7 mg, 2.38 mmol, 0.94 eq, trisHCl salt) in toluene (10.00 mL), Pd2(dba)3 (348.9 mg, 381.0 umol, 0.15 eq), XPhos (544.9 mg, 1.14 mmol, 0.45 eq), and NaOu (610.2 mg, 6.35 mmol, 2.50 eq) was added. The resulting mixture was de-gassed and purged with nitrogen, then heated to 110C under nitrogen atmosphere for 7 hours until there was no more starting material as indicated by LCMS analysis. The reaction mixture was cooled to room temperature, and filtered over celite, and washed with CH2CI2 (10 mL) and EtOAc (10 mL). The organic phase was then concentrated under vacuum after which the resulting residue was purified by silica gel column chromatography (5: 1 petroleum ethenEtOAc), and further purified by prep-TLC (7: 1 CH2Cl2/MeOH) to afford the compound 231 (90.0 mg, 270.5 umol, 11% yield, 90% purity) as a brown yellow solid.

Molecular Weight:197.03
XLogP3:1.8
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:17.3
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes