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With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; at 60.0℃; under 2999.54 Torr; for 2.0h;
30 ml of cone. HCI and 0.750 g of 10% Pd/C are added to a solution of 15.770 mmol of ethylimidazo[1,5-a]pyridine-5-carboxylate [76292-67-6] in 100 ml of ethanol. The reaction mixtureis subsequently hydrogenated at 58 psi and 60C for 2 hours. The catalyst is filtered off viaHyflo and the filtrate is concentrated. The crude title compound is obtained from the residueas an amber-coloured oil. Rf = 0.37 (toluene/methanol = 85:15); Rt = 4.19.
With trichlorophosphate; In toluene; at 80.0℃; for 2.0h;
To a solution of ethyl 6-(formamidomethyl)picolinate (23 g, 110 mmol) in toluene (400 mL) was added POC13 (23 mL) at room temperature and the mixture was heated at 80C for 2 hours. Then cooled to room temperature and evaporated the solvent under reduced pressure before HC1 (400 mL, iN) was added to the residue, extracted with EA (200 mL*2), isolated theaqueous layer, adjusted pH=7-8 with saturated aqueous of NaOH before extracted with EA (400 mL*2), combined the organic layers, evaporated the solvent under reduced pressure to give crude solid (13g in 62% yield) as a brown solid. ‘H NMR (DMSO-d6) ö 9.13 (s, 1H), 7.98 (d, 1H,J=8.8 Hz), 7.67 (s, 1H), 7.64 (dd, 1H,J=6.8 Hz), 4.24 (q, 2H,J=6.4 Hz), 1.39 (t, 3H,J=7.2 Hz).
With sodium tetrahydroborate; In ethanol; at 80.0℃; for 1.0h;
To a solution of ethyl imidazo[1,5-a]pyridine-5-carboxylate (36 g, 189 mmol) in EtOH (1L) was added batch wise of NaBH4 (14.3 g, 379 mmol) at 80C and the mixture was stirred at 80C for lh. Then evaporated the solvent under reduced pressure and water (100 mL) was added to the residue, extracted with EA (400 mL*2), combined the organic layer, dried over Na2504,filtered to remove the solid, the filtrate was evaporated under reduced pressure to give crudeproduct (27.9 g) and this crude product was used for next step without further purification. ‘HNMR (DMSO-d6) ö 8.33 (s, 1H), 7.53 (d, 1H, J=8.8 Hz), 7.79-6.83 (m, 1H), 6.68 (dd, 1H, J=6.4Hz), 5.73(s, 1H), 4.76 (s, 2H).
imidazo[1,5-a]pyridine-5-carboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20.0℃;
To a solution of ethyl imidazo[1,5-a]pyridine-5-carboxylate (2.0 g, 10.5 mmol,Compound of Step 6 in Example A001) in a mixture of THF (20 mL) and water (5 mL) was added lithium hydroxide hydrate (881 mg, 2 eq) at room temperature and the mixture was stirred overnight. Evaporated the solvent under reduced pressure and water (80 mL) was added to the residue and adjust pH=6-7 with HC1 (4 N) and the yellow precipitate was collected by filtration to give 1.lg in 65% yield. ‘H NMR (DMSO-d6) ö 9.20 (s, 1H), 7.90 (d, 1H, J=9.2 Hz), 7.61 (s, 1H), 7.57 (dd, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=9.2 Hz).
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