4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER synthesis
- Product Name:4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER
- CAS Number:833486-94-5
- Molecular formula:C12H17BN2O4
- Molecular Weight:264.09
875-51-4
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73183-34-3
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$6.00/5g
833486-94-5
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$21.00/100mg
Yield:833486-94-5 92%
Reaction Conditions:
with potassium acetate;palladium diacetate in N,N-dimethyl-formamide at 85; for 5 h;
Steps:
5.a
Example 5; N-(5-{2-[(2-Chlorophenyl)amino]-6-oxo-1,6-dihydro-4-pyrimidinyl}-1H-benzimidazol-2-yl)-2-thiophenecarboxamide (Ie); a. 2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (VI) To a solution of 4-bromo-2-nitroaniline (10.0 g, 46.0 mmol), bis(pinacolato)diboron (12.8 g, 50.6 mmol) and potassium acetate (13.5 g, 138.0 mmol) in DMF (175 mL), palladium(II) acetate (309.8 mg, 1.38 mmol) was added and stirred at 85° C. for 5 hrs under argon. The mixture was concentrated, water was poured into it and extracted with CH2Cl2. The organic extract was dried over Na2SO4, and then concentrated. Recrystallizations from CH2Cl2/hexane gave the title compound (16.1 g, 92%). 1H-NMR (400 MHz, d6-DMSO) δ 8.27 (s, 1H), 7.70 (s, 2H), 7.55 (d, 1H), 6.98 (d, 1H) and 1.27 (s, 12H).
References:
Hasegawa, Masaichi;Takada, Mio;Washio, Yoshiaki US2007/117818, 2007, A1 Location in patent:Page/Page column 11-12
89-63-4
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73183-34-3
555 suppliers
$6.00/5g
833486-94-5
100 suppliers
$21.00/100mg