Methyl triflate → 5-(2-Bromo-5-(trifluoromethyl)phenyl)-1-methyl-1,2,3,6-tetrahydropyridine

A solution of 3-(2-bromo-5-(trifluoromethyl)phenyl)pyridine (2.000 g, 6.62 mmol) in 13 mL DCM was treated with methyl trifluoromethanesulfonate (0.802 ml, 7.28 mmol) and was allowed to stir at room temperature for one hour. LC/MS showed mostly product so the reaction mixture was treated with sodium triacetoxyborohydride (4.21 g, 19.86 mmol) and was allowed to stir at room temperature overnight. LC/MS showed only a small amount of product, so the reaction mixture was concentrated then taken back up in 12 mL THF and cooled to 0° C. lithium borohydride (3.31 ml, 6.62 mmol) was added, and the reaction mixture was allowed to stir for one hour. LC/MS showed mostly product, so the reaction mixture was quenched with 7N ammonia in MeOH and was allowed to stir over the weekend. The reaction mixture was poured into water and was extracted with DCM. The organics were concentrated the purified directly by reverse phase column chromatography yielding 5-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1,2,3,6-tetrahydropyridine (0.860 g, 2.69 mmol, 40.6% yield) with impurities. m/z (ESI) 321.9 (M+H)+.

1. stirringto stir at room temperature overnight
2. concentrationso the reaction mixture was concentrated
3. additionwas added
4. stirringto stir for one hour
5. customso the reaction mixture was quenched with 7N ammonia in MeOH
6. stirringto stir over the weekend
7. additionThe reaction mixture was poured into water
8. extractionwas extracted with DCM
9. concentrationThe organics were concentrated the
10. custompurified directly by reverse phase column chromatography

ORD 기록

ord-1f2e73802f754f06a0dc0ed95ee13cfd

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09012443B2