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CAS No. : | 89694-46-2 | MDL No. : | MFCD06659858 |
Formula : | C7H8BClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REFXAANPQCJZRY-UHFFFAOYSA-N |
M.W : | 186.40 | Pubchem ID : | 17750233 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
84% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 4h;Heating / reflux; | Example 50 Synthesis of 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (33.47 mmol, 1.0 equiv), 1-chloro-4-methoxy-2-boronic acid (50.21 mmol, 1.5 equiv), Pd(PPH3)4 (3.347 mmol, 0.1 equiv), and Na2CO3 (133.9 mmol, 4.0 equiv) dissolved in DME/EtOH/water 6:1:1 and refluxed at 100° C. under an argon blanket for 4 h. The reaction was cooled to room temperature and diluted with 100 mL DCM and filtered. Precipitate recovered was suspended in water, filtered and rinsed with ether. Precipitate afforded product: 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, a green solid (8.37 g, 84percent yield). Rf=0.85 (9:1 DCM/MeOH). 1H NMR (DMSO-d6): delta 3.35 (s, 6H), 7.01 (dd, J=8.8 Hz, J=3.0, 1H), 7.09 (d, J=3.0 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.75 (bm, 2H). MS (ES+) m/z=303. LC retention time 3.03 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | In N,N-dimethyl-formamide; acetonitrile; at 85℃; for 0.5h; | A mixture of 2-chloro-5-methoxyhenylboronic acid (43 mg, 0.23 mmol), Intermediate 1 (72 mg, 0.2 mmol) and glyoxylic acid monohydrate (21 mg, 0.23 mmol) in acetonitrile (0.7 mL) and DMF (0.07 mL) was heated at 85° C. for 30 min in a Microwave Reactor. The crude product was purified by flash column chromatography (CH2Cl2:MeOH=100:15) to give 28 mg (25percent) of 77A as a solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 1.16 (s, 18 H) 3.24 (s, 3 H) 5.55 (s, 1 H) 6.57 (d, J=2.20 Hz, 1 H) 6.75-6.84 (m, 2 H) 7.00 (d, J=3.08 Hz, 1 H) 7.10-7.20 (m, 1 H) 7.27 (d, J=9.23 Hz, 1 H) 7.32 (d, J=5.27 Hz, 1 H) 7.54 (d, J=9.23 Hz, 1 H) 7.93 (d, J=6.15 Hz, 1 H); LC MS 558 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 70 - 75℃; for 2h; | Method D To a suspension of <strong>[1458-01-1]3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester</strong> (10.9 g, 53.7 mmol) in 220 ml 1,4-dioxane and water (40 ml) was added 2-chloro-5-methoxybenzene boronic acid (20 g, 107 mmol), cesium carbonate (17.5 g, 53.7 mmol) and palladium tetrakis(triphenylphosphine) (620 mg, 0.54 mmol). The reaction was heated in an oil bath at 70-75° C. for 2 hours. The reaction was then cooled and poured into 500 ml water. The resulting slurry was stirred for 10 minutes before filtering under vacuum. The beige solid collected was then slurried in 100 ml methanol, stirred for 15 minutes, then filtered, washing the filter cake with methanol and vacuum drying to afford 17.4 g of the title product. 1H-NMR (d6-DMSO): NMR (DMSO): 3.65 (s, 3H), 3.75 (s, 3H), 6.4 (br s 2H), 6.9 (d, 1H), 7.0 (dd, 1H), 7.05 (br, s, 2H), 7.4 (d, 2H). LCMS Rt=3.74 min MS m/z 309 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In ethanol; water; toluene; at 20℃;Heating / reflux;Product distribution / selectivity; | To 3-iodopyridine-2,6-diamine (Preparation 44, 3.0 g, 12.8 mmol), 5-methoxy-2- chlorophenylboronic acid (2.62 g, 14.0 mmol), sodium carbonate (1.49 g, 14.0 mmol), ethanol (15 ml), water (15 ml) and tris(dibenzylideneacetone)dipalladium (0) (175 mg,0.19 mmol) at ambient temperature under a nitrogen atmosphere was added tri- <n="142"/>terfbutylphosphine (1M in toluene, 0.574 ml, 0.574 mmol). The brown mixture was heated to reflux and maintained until reaction completion by HPLC. The reaction was cooled to ambient and the ethanol removed by vacuum distillation. 2- methyltetrahydrofuran (30 ml) was then added and the biphasic mixture filtered over arbocel.(TM)., extracted with saturated aqueous sodiumhydrogencarbonate (20 ml) and separated. The organic layer was extracted five times with 10percent w/v citric acid (20 ml), then to the combined aqueous layers was added 2-methyltetrahydrofuran (30 ml) then 5M sodium hydroxide until obtaining a pH>10. The layers were separated and the upper organic layer was concentrated to dryness in vacuo obtaining product as a beige solid 2.90 g (91percent yield). |
55% | With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 19h;Product distribution / selectivity; | To a suspension of 3-iodopyridine-2,6-diamine (Preparation 44, 2 g, 8.51 mmol) in 1 ,4- dioxane (10 ml) and water (5 ml) was added <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol), cesium carbonate (2.77 g, 8.51 mmol) and palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol). The reaction was purged with nitrogen and heated at 80QC for 20 minutes. Three further portions of palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol) and <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol) were added at 20 minute intervals. The reaction was heated at 8O0C for 18 hours before concentrating in vacuo. The residue was taken up in ethyl acetate (20 ml) and washed with a saturated aqueous solution of brine (20 ml) before drying over Na2SO4 and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluting with 50:50 to 100:0 ethyl acetate-.pentane to afford the title compound as a brown foam (1.157 g, 55percent yield). MS m/z 250 [MH]+1HNMR (CDCI3): 3.79 (s, 3H), 4.23 (br s, 2H), 4.32 (br s, 2H), 6.00 (d, 1 H), 6.86 (m,2H), 7.14 (d, 1 H), 7.38 (d, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | EXAMPLE 92 4-Amino-8-(2-chloro-5-methoxyphenyl)-7-fluoro-cinnoline-3-carboxylic acid propylamide The title compound was prepared from 4-amino-7-fluoro-8-iodo-N-propylcinnoline-3-carboxamide (250 mg, 0.67 mmol) and <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (279 mg, 1.50 mmol) according to Method A to afford a solid (181 mg, 72percent). 1H NMR (500.333 MHz, CDCl3) delta 8.41 (s, 1H), 7.90 (dd, J=9.1, 5.1 Hz, 1H), 7.49 (t, J=8.7 Hz, 1H), 7.41 (dd, J=6.9, 2.7 Hz, 1H), 6.94-6.92 (m, 2H), 3.79 (s, 3H), 3.44 (q, J=6.7 Hz, 2H), 1.65 (sextet, J=7.2 Hz, 2H), 0.99 (t, J=7.3 Hz, 3H). MS APCI, m/z=389/391 (M+H). HPLC 2.13 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-chloro-succinimide; In acetonitrile; at 20℃; | Method 12B; Method 12A was used except NCS was substituted for NBS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere; | Synthesis of intermediate 2 6-(2-Chloro-5-methoxy~phenyi)-quinazolin-2- ylamine; To a solution of 2-chloro-5-methoxy boronic acid (14.42g, 77.34 mmol, 1.5eq), 6-Bromo-quinazolin~2~ylamine ( 11.55g, 51.56 mmol, leq) and Na2CO3 (21.86g, 206.23 mmol, 4eq) in a mixture of 120ml DMF/3ml EtOH/30m. H2O, was added 2.311g (5.16 mmol, 0.1 eq) of tetrakis(tpiphenylphospine) palladium. The reaction was refluxed(1000C) for 2 hours under argon. It was then cooled off to room temperature to extract the product by DCM and brine. The product is then washed with water and ether, then dried to give 9.010 g (32 mmol, 61percent) of a pale yellow powder. |
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