Piperidine → (5-Bromopyridin-2-yl)(piperidin-1-yl)methanone

5-bromo-2-pyridinecarboxylic acid (501 mg, 2.480 mmol, available from Apollo) was mixed with HATU (2358 mg, 6.20 mmol), DIPEA (1.625 mL, 9.30 mmol) and piperidine (0.307 mL, 3.10 mmol), dissolved in N,N-dimethylformamide (DMF) (22.5 mL) and stirred under nitrogen for 18 hours. The reaction was partitioned between distilled water (30 mL) and DCM (100 mL). The aqueous layer was extracted with DCM (2×70 mL) and the organic fractions were combined, washed (brine (2×50 mL)), dried (sodium sulfate), filtered and evaporated to dryness to give a dark brown solid (2.43 g). The crude product was purified on a 40+M Biotage silica column, eluting with cyclohexane:EtOAc (1:0 to 3:2, 19 CV). Product-containing fractions were evaporated to dryness to give a dark yellow solid (573 mg). LCMS (Method C): Rt=0.83, MH+=271

1. customThe reaction was partitioned
2. distillationbetween distilled water (30 mL) and DCM (100 mL)
3. extractionThe aqueous layer was extracted with DCM (2×70 mL)
4. washwashed (brine (2×50 mL))
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. customevaporated to dryness

ORD record

ord-475ce7afecee45e89bf773b6eb0778d1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697725B2