[ CAS No. 1086378-35-9 ]

Name: Methyl benzo[d]oxazole-7-carboxylate
Brand: Ambeed
SKU: A102984
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Quality Control of [ 1086378-35-9 ]

COA GC NMR CNMR HPLC LC-MS

SDS

TPSA :Topological Polar Surface Area	52.3	H-Bond Acceptor Count :	4
XLogP3 :	1.6	H-Bond Donor Count :	0
SP3 :	0.11	Rotatable Bond Count :	2

Yield	Reaction Conditions	Operation in experiment
91%	With ytterbium(III) triflate In toluene at 100℃; for 1.00 h; Microwave irradiation	Methyl 3-amino-2-hydroxybenzoate (1.69 g, 10.13 mmol) was suspended in toluene (2 mL) in a microwave vial. HC(OEt)₃ (1.80 g, 12.15 mmol) and Yb(OTf)₃ (0.003 g, 0.005 mmol) was added and the reaction was heated at 100 °C for 1 hour in the microwave. The reaction mixture was evaporated and purified by flash chromatography (petroleum ether/EtOAc 4:1) to give the title compound (1.63 g, 91percent) as pale yellow crystals. mp. 116 – 118 °C (Litt⁹. 77 °C). ¹H NMR (300 MHz, CDCl₃) δ 8.21 (s, 1H), 8.04 (dd, J = 7.8, 1.2 Hz, 1H), 7.99 (dd, J = 8.0, 1.2 Hz, 1H), 7.44 (dd, J = 8.0, 7.8 Hz), 3.76 (s, 3H). ¹³C NMR (75 MHz, CDCl₃) δ 180.9, 164.4, 153.4, 141.4, 128.0, 125.6, 124.5, 115.4, 52.6

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937

Yield	Reaction Conditions	Operation in experiment
93%	With toluene-4-sulfonic acid; for 1.0h;Reflux;	A solution of methyl 3-amino-2-hydroxybenzoate (1 g, 5.99 mmol) and p-toluenesulfonic acid (0.1 g, 0.581 mmol) in trimethylorthoformate (50 mL) was refluxed for 1 hour. Volatiles were evaporated under reduced pressure. The crude was purified by column chromatography on silica gel using 20:1 DCM:EtOAc as eluent to give methyl benzo[d]oxazole-7-carboxylate (0.99 g, 93%). UPLC-MS (Acidic Method, 2 min): rt 0.79 min, m/z 178.1 [M+H]+

Reference： [1]Patent: WO2020/43880,2020,A1.Location in patent: Page/Page column 14; 18; 19; 20; 26; 28

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium(0); lithium tert-butoxide; In 1,4-dioxane; at 20℃; for 0.75h;Inert atmosphere;	A solution of <strong>[1086378-35-9]methyl benzo[d]oxazole-7-carboxylate</strong> (0.5 g, 2.82 mmol), 1-iodo-4-nitrobenzene (0.88 g, 3.53 mmol), lithium tert-butoxide (0.45 g, 5.64 mmol), tetrakis(triphenyl phosphine)palladium(0) (0.16 g, 0.141 mmol) in dioxane under a nitrogen atmosphere was stirred at room temperature for 45 minutes. The resulting thick suspension was diluted with EtOAc, washed with water, organics washed with brine, dried over Na2SO4, decanted and solvent removed under vacuum. The crude was purified by column chromatography on silica gel using 20:1 to 5:1 Hexane:EtOAc as eluent to give methyl 2-(4-nitrophenyl)benzo[d]oxazole-7-carboxylate (0.4 g, 48%). UPLC-MS (Acidic Method, 2 min): rt 1.11 min, m/z 299.0 [M+H]+

Reference： [1]Patent: WO2020/43880,2020,A1.Location in patent: Page/Page column 14; 18; 19; 20; 26; 27; 28

3
[ 1086378-35-9 ]
N-(4-(7-(2-hydroxypropan-2-yl)benzo[d]oxazol-2-yl)phenyl)-1-methyl-1H-pyrazole-5-carboxamide [ No CAS ]