2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amine

HRID 1486926Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[N:11][CH:12]=1.[CH3:20][C:21]1([CH3:32])[C:25]([CH3:27])([CH3:26])[O:24][B:23](OC(C)C)[O:22]1>C1COCC1>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([B:23]2[O:24][C:25]([CH3:27])([CH3:26])[C:21]([CH3:32])([CH3:20])[O:22]2)=[CH:12][N:11]=1

Participants

Conditions

Temperature: 18 °C

Procedure

Butyllithium (2.5N, 4.8 mL, 50.96 mmol) was added to a solution of 3-(5-bromopyridin-2-yl)oxy-N,N-dimethylpropan-1-amine (2.07 g, 7.99 mmol) and 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (2.79 g, 15.00 mmol) in THF (20 mL) at −78° C. over 10 minutes under an inert atmosphere. The resulting solution was stirred for 4 h at 18° C. The reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride then partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was concentrated in vacuo and the residue purified by FCC, eluting with EtOAc/petroleum ether (1:3) to afford the desired material (270 mg, 11%) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+=225.

Workup

customThe reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride
customthen partitioned between EtOAc (100 mL) and water (100 mL)
concentrationThe organic layer was concentrated in vacuo
customthe residue purified by FCC
washeluting with EtOAc/petroleum ether (1:3)

Sources & evidence

ORD record: ord-3e069e9040904f1999813d7bf5c39f01
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428503B2

Reaction notes

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