2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-[3-(1-Azetidinyl)propoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 1486942Notes

Reaction equation

HRID 1486942 reaction equation
C([Li])CCC.[N:6]1([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:9][CH2:8][CH2:7]1.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C1COCC1>[N:6]1([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([B:25]3[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]3)=[CH:16][N:15]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1184986242-[3-(Azetidin-yl)propoxy]-5-bromopyridineHCID 178418339Butyllithium

Product 1

HCID 1235709422-[3-(1-Azetidinyl)propoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (4.65 mL, 11.62 mmol) was added to 2-[3-(azetidin-yl)propoxy]-5-bromopyridine (2.1 g, 7.74 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.161 g, 11.62 mmol) in THF (50 ml) at −78° C. over a period of 10 minutes and the resulting solution stirred at −78° C. for 1 h. The reaction was quenched with sat. Na2SO4 (10 mL) and the solvent removed in vacuo. The residue was dissolved in DCM (100 mL), dried over Na2SO4, filtered and evaporated to afford the desired material (2.00 g, 81%) as a white solid. Mass Spectrum: m/z (ES+)[M+H]+=319.

Workup

  1. customThe reaction was quenched with sat. Na2SO4 (10 mL)
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in DCM (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-657cffa3b198461c959ae27128c22a06
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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