Related Products of 131747-69-8 , The common heterocyclic compound, 131747-69-8, name is 2-Fluoroisonicotinaldehyde, molecular formula is C6H4FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 132Preparation of 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin- 4-yl)methylamino)-5a,5b,8,8,lla-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1. Preparation of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- ((2-fluoropyridin-4-yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate.To a solution of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- amino-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, HCl (318 mg, 0.548 mmol) in DCE (10 mL) was added glacial acetic acid (0.314 mL, 5.48 mmol), sodium acetate (67.4 mg, 0.822 mmol), 2-fluoropyridine-4-carboxaldehyde (206 mg, 1.644 mmol) and 4A molecular sieves. The reaction mixture was heated to 65 C for 18 h. To the reaction mixture was added sodium triacetoxyhydroborate (581 mg, 2.74 mmol) and the resulting mixture was heated to 65 C for 7.5 h, then the mixture was left at rt for 48 h. The reaction was diluted with DCM (50 mL) and washed with saturated aHC03 (20 mL). The aqueous layer was extracted with DCM (2 x 25 mL). The combined organic layer was dried over MgS04, filtered and concentrated. The resulting dark brown residue was dissolved in THF (3 mL) and MeOH (0.6 mL), filtered and purified by reverse phase preparative HPLC using HPLC method 3 to give methyl 4- ((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin-4- yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, TFA (218.4 mg, 0.285 mmol, 52.0% yield) as a white solid. LCMS: m/e 653.4 (M+H)+, 2.69 min (method 6).
The synthetic route of 131747-69-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; LIU, Zheng; SWIDORSKI, Jacob; SIN, Ny; VENABLES, Brian Lee; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; WO2012/106190; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem