TERT-BUTYL 3-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOL-1-YL)AZETIDINE-1-CARBOXYLATE synthesis
- 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
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73183-34-3
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877399-35-4
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$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
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141699-58-3
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$6.00/250mg
877399-35-4
73 suppliers
$85.00/100mg
269410-08-4
398 suppliers
$5.00/1g
254454-54-1
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$15.00/1g
877399-35-4
73 suppliers
$85.00/100mg
141699-55-0
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$6.00/1g
877399-35-4
73 suppliers
$85.00/100mg
141699-58-3
114 suppliers
$6.00/250mg
877399-35-4
73 suppliers
$85.00/100mg