ChemicalBook CAS DataBase List TERT-BUTYL 3-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOL-1-YL)AZETIDINE-1-CARBOXYLATE

TERT-BUTYL 3-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOL-1-YL)AZETIDINE-1-CARBOXYLATE synthesis

5synthesis methods

Product Name:TERT-BUTYL 3-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOL-1-YL)AZETIDINE-1-CARBOXYLATE
CAS Number:877399-35-4
Molecular formula:C17H28BN3O4
Molecular Weight:349.23

877399-34-3 Synthesis

1-Boc-3-(4-BroMo-1H-pyrazol-1-yl)azetidine

877399-34-3
59 suppliers
$54.00/100mg

73183-34-3
566 suppliers
$6.00/5g

TERT-BUTYL 3-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOL-1-YL)AZETIDINE-1-CARBOXYLATE

877399-35-4
70 suppliers
$85.00/100mg

Yield: 97%

Reaction Conditions:

with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ in dimethyl sulfoxide at 80;

Steps:

59
tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3-dioxoborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (2-8): A reaction mixture of compound (2-6) (225 mg, 0.74 mmol) and bis(pinacolate)diboron (2-7, 227 mg, 0.89 mmol) with KOAc (247 mg, 2.52 mmol) in 3 mL of DMSO was purged with N₂ for 15 minutes, then PdCl₂(dppf)₂CH₂Cl₂ (30 mg, 2.52 mmol) was added. The resulting mixture was stirred at 80° C. under N₂ for overnight. After it cooled down to room temperature, the mixture was filtered through Celite pad and washed well with EtOAc. The filtrate was extracted with H₂O (2*50 mL), brine (50 mL). The organic layer was dried (Na₂SO₄), then concentrated by vacuum. The residue was then filtered through silica gel pad, eluted with hexane:EtOAc/3:2. The filtrate was concentrated by vacuum to give 250 mg of 2-8) as a clear oil (97% yield). ¹H NMR (400 MHz, chloroform-D) δ ppm 1.18-1.27 (m, 9H) 1.28-1.34 (m, 6H) 1.41-1.49 (m, 6H) 4.22-4.33 (m, 2H) 4.36 (t, J=8.59 Hz, 2H) 4.98-5.13 (m, 1H) 7.83 (s, 2H).

References:

AGOURON PHARMACEUTICALS, INC. US2006/46991, 2006, A1 Location in patent:Page/Page column 57-58

269410-08-4 Synthesis