Acetyl chloride → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-one

HRID 634421Notes

Reaction equation

HRID 634421 reaction equation
Cl.[CH3:2][C:3]1([CH3:16])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)[O:4]1.[C:17](Cl)([CH3:19])=[O:18]>C(Cl)Cl.CCOC(C)=O>[CH3:9][C:7]1([CH3:8])[C:3]([CH3:16])([CH3:2])[O:4][B:5]([C:10]2[CH2:11][CH2:12][N:13]([C:17](=[O:18])[CH3:19])[CH2:14][CH:15]=2)[O:6]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 497610841,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride

Product 1

HCID 567376781-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-oneYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (Intermediate G3, 1.4 g, 5.70 mmol) was suspended in DCM (15 mL) at 0° C., then TEA (2.384 ml, 17.10 mmol) and AcCl (0.405 ml, 5.70 mmol) were added The reaction was allowed to warm up to rt and stirred for further 30 min, then the reaction volume was reduced to 1/3 of the initial volume and the residue diluted with AcOEt (150 ml). Organic phase was washed twice with water, once with 0.2 M HClaqueous and once with saturated NaClaqueous, anhydrified over Na2SO4 and solvent removed under reduced pressure to give the title compound (1.24 g, 87% yield) as yellowish solid.

Workup

  1. washOrganic phase was washed twice with water, once with 0.2 M HClaqueous
  2. customonce with saturated NaClaqueous, anhydrified over Na2SO4 and solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4b176ca573694fb6a2023f3f4354a0ca
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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