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CAS No. : | 1257792-67-8 | MDL No. : | MFCD18383414 |
Formula : | C13H18BNO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JKHCSEPRRUKNJR-UHFFFAOYSA-N |
M.W : | 279.10 | Pubchem ID : | 57483800 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Step 1 2-(2-Methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid; 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (1.7 g, 6.08 mmol), <strong>[1194374-25-8]2-bromo-5-methyl-thiazole-4-carboxylic acid</strong> (900 mg, 4.05 mmol), tetrakis (triphenylphosphine)palladium (233 mg, 0.2 mmol) and sodium carbonate (1.29 g, 12.16 mmol) were dissolved in 30 mL of 1,4-dioxane. The reaction mixture was heated to reflux for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 20 mL of hydrochloric acid (1 N) and 30 mL of ethyl acetate. The separated organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain the title compound 2-(2-methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid 47a (310 mg, yield 26%) as a yellow solid. MS m/z (ESI): 292.6 [M-1] 1H NMR (400 MHz, DMSO-d6): delta 13.45 (br, 1H), 8.58 (dd, J = 8.0, 1H), 8.14 (dd, J = 8.0,1H), 7.52 (t, J = 8.0, 1H), 3.93 (s, 3H), 2.71 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.7% | Step 2 4-(3-nitro-2-methoxy-phenyl)-furan-2-carboxylic acid 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 6a (4 g, 14.34 mmol), <strong>[3439-02-9]4-bromo-furan-2-carboxylic acid</strong> 28b (2.18 g, 11.47 mmol), tetrakis(triphenylphosphine)palladium (829 mg, 0.717 mmol) and potassium carbonate (3.96 g, 28.68 mmol) were dissolved in the solvent mixture of 80 mL of 1,4-dioxane and 30 mL of water. The reaction mixture was heated to reflux for 2.5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was adjusted to pH 3 with 1 N hydrochloric acid and then extracted with ethyl acetate (80 mL×3). The combined organic extracts were concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 4-(3-nitro-2-methoxy-phenyl)-furan-2-carboxylic acid 28c (3.42 g, yield 90.7%) as a brown oil. MS m/z (ESI): 261.8 [M-1] | |
90.7% | Step 2 4-(3-nitro-2-methoxy-phenyl)-furan-2-carboxylic acid 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane 4d (4 g, 14.34 mmol), <strong>[3439-02-9]4-bromo-furan-2-carboxylic acid</strong> 22b (2.18 g, 11.47 mmol), tetrakis (triphenylphosphine)palladium (829 mg, 0.717 mmol) and potassium carbonate (3.96 g, 28.68 mmol) were dissolved in the solvent mixture of 80 mL of 1,4-dioxane and 30 mL of water. The reaction mixture was heated to reflux for 2.5 hours. The mixture was adjusted to pH 3 with 1 M hydrochloric acid and then extracted with ethyl acetate (80 mLx3). The combined organic extracts were concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 4-(3-nitro-2-methoxy-phenyl)-furan-2-carboxylic acid 22c (3.42 g, yield 90.7%) as a brown oil. MS m/z (ESI): 261.8 [M-1] | |
90.7% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 2.5h;Reflux; | 2-(2-methoxy-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan 4d (4g, 14.34mmol), <strong>[3439-02-9]4-bromofuran-2-carboxylic acid</strong> (2.18g, 11.47mmol), tetrakis(triphenylphosphine)palladium (829mg, 0.717mmol) and potassium carbonate (3.96g, 28.68mmol) dissolved in a mixed solvent 80mL 1,4-dioxane and 30mL of water were heated at reflux for 2.5 hours. The reaction was washed with 1M hydrochloric acid to a pH of about 3 and extracted with ethyl acetate (80mL × 3). The organic phase was concentrated under reduced pressure to give the title product after column chromatography 4-(3-nitro-2-methoxyphenyl)furan-2-carboxylic acid 22c (3.42g, brown oil). Yield: 90.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 40 h / 70 °C 2: potassium acetate / tetrakis(triphenylphosphine) palladium(0) / etheroxalic acid dimethyl ether / 17 h / Reflux | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 40 h / 70 °C 2: potassium acetate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 17 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 19: (Z)-4-{2-hydroxy-3-[N'-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-thiophene-2-carboxylic acid bis-(ethanolamine); Step 1; 4-(3-Nitro-2-methoxy-phenyl)-thiophene-2-carboxylic acid; 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4d (0.81 g, 2.9 mmol), <strong>[16694-18-1]4-bromo-thiophene-2-carboxylic acid</strong> (0.3 g, 1.45 mmol), tetrakis (triphenylphosphine)palladium (80 mg, 0.073 mmol) and sodium carbonate (0.31 g, 2.9 mmol) were dissolved in a solvent mixture of 20 mL of 1,4-dioxane and 10 mL of water. The reaction was heated to reflux for 0.5 hours. The mixture was adjusted to pH 3 with 1 N hydrochloric acid and extracted with ethyl acetate (20 mLx3). The combined organic extracts were concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 4-(3-nitro-2-methoxyphenyl)-thiophene-2-carboxylic acid 19a (0.54 g) as a brown oil, which was directly used in the next step. MS m/z (ESI): 277.6 [M-1] | ||
0.54 g | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; for 0.5h;Reflux; | 2-(2-methoxy-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan 4d (0.81g, 2.9 mmol), <strong>[16694-18-1]4-bromothiophene-2-carboxylic acid</strong> (0.3g, 1.45mmol), tetrakis(triphenylphosphine)palladium (80mg, 0.073mmol), and sodium carbonate (0.31g, 2.9mmol) dissolved in a mixed solvent 20mL 1,4-dioxane and 10mL of water was heated at reflux for 0.5 hours. The reaction solution was adjusted with 1M hydrochloric acid to pH = 3 and was extracted with ethyl acetate (20mL × 3). The combined organic phases was concentrated under reduced pressure column chromatography to give 4-(3-nitro-2-methoxyphenyl)thiophene-2-carboxylic acid 19a (0.54g, brown oil), directly to the next step reaction. |