* 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.
In a round bottom flask, a mixture of 7-nitroquinoxalin-2-ol (3) (12.73 g, 67 mmol) in 20 mL of phosphoryl chloride(POCl3) was refluxed for 3 h. Then, the mixture wasslowly poured into a stirred mixture of ice and water. Theprecipitate was filtrated and washed with water to obtain13.43 g of a red/cherry solid. Yield 96percent; mp 183-186 °C(lit. 185-189 °C);5 ATR/FTIR ν / cm-1 3092, 3048, 1682,1525, 1350, 740; 1H NMR (200 MHz, DMSO-d6) δ 9.22(s, 1H, H3), 8.88 (d, 1H, J 3.0, H8), 8.59 (dd, 1H, J 2.0, 9.0, H6), 8.39 (d, 1H, J 9.0, H5); 13C NMR (100 MHz,DMSO-d6) δ 149.2, 148.8, 148.3, 142.8, 140.2, 130.9,124.1, 123.9; DEPT-135 (100 MHz, DMSO-d6) δ 148.8,130.9, 124.1, 123.9; MS 209.1 + 211.1.
Reference:
[1] Journal of the Brazilian Chemical Society, 2017, vol. 28, # 10, p. 1874 - 1878
[2] Tetrahedron Letters, 1991, vol. 32, # 10, p. 1311 - 1314
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6169 - 6186
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4508 - 4522
2
[ 109541-16-4 ]
[ 55686-94-7 ]
Reference:
[1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670
3
[ 1196-57-2 ]
[ 55686-94-7 ]
Reference:
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4508 - 4522
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6169 - 6186
[3] Journal of the Brazilian Chemical Society, 2017, vol. 28, # 10, p. 1874 - 1878
4
[ 6639-87-8 ]
[ 55686-94-7 ]
Reference:
[1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670
5
[ 95-54-5 ]
[ 55686-94-7 ]
Reference:
[1] Journal of the Brazilian Chemical Society, 2017, vol. 28, # 10, p. 1874 - 1878
6
[ 89898-96-4 ]
[ 55686-94-7 ]
Reference:
[1] Yakugaku Zasshi, 1959, vol. 79, p. 658[2] Chem.Abstr., 1959, p. 21979
[3] Justus Liebigs Annalen der Chemie, 1953, vol. 579, p. 212,220
[4] Journal of the Chemical Society, 1956, p. 26,27
[5] Journal of the Chemical Society, 1961, p. 1246,1250
7
[ 55686-94-7 ]
[ 89898-96-4 ]
Reference:
[1] Journal of the Chemical Society, 1956, p. 26,27
[2] Justus Liebigs Annalen der Chemie, 1953, vol. 579, p. 212,220
[3] Yakugaku Zasshi, 1959, vol. 79, p. 658[4] Chem.Abstr., 1959, p. 21979
With tin(II) chloride dihdyrate; In ethyl acetate; for 2h;Reflux;
To a suspension of nitro compound VI (14.36 g,68.5 mmol, 1 equiv.) in AcOEt (300 mE) is added SnCl2.2H20 (45.5 g, 239.9 mmol, 3.5 equiv.), then the reaction mixture is refluxed for 2 h. Afier cooling, 50% NaOH (6 equiv., 480 mmol) is added slowly at 00 C. and the reaction mixture is filtered on a silica gel pad and then eluted with hot acetone. After concentration, the residue is purified by recrystallisation with CHC13/petroleum ether to afford compound Had in the form of a yellow solid (9.65 g, 78%). ?H NMR (300 MHz, CDC13) oe ppm: 4.30 (brs, 2H), 7.03 (d, J=1.7 Hz, 1H), 7.15 (dd, J=8.8, 1.7 Hz, 1H), 7.85 (d, J=8.8 Hz, 1H), 8.47 (s, 1H). ?3C NMR (75 MHz, CDC13) oe ppm:107.2, 121.7, 130.3, 135.98, 140.3, 144.2, 147.7, 149.1. High-resolution mass (ESI): mlz calculated for [M+H] C8H7N3C1: 180.0329; mlz measured: 180.0326.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100.0℃; for 7.0h;Inert atmosphere;
2-Chloro-7-nitroquinoxaline (27.8g, 133mmol), 1 -methyl-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazole (30.4g, 146mmol), 2M Na2C03 aqueous solution (66.3ml_, 133mmol) in ethylene glycol dimethyl ether (330ml_) were degassed with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (1.5g, 1 .33mmol) was added and the reaction mixture was heated at 100C for 7 hours. The reaction was poured into water. The precipitate was filtered off, taken-up with EtOAc, then filtered and dried under vacuum to give 31.4g (93%) of intermediate 4 (yellow solid). MP=231 C (DSC).
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); In 1,4-dioxane; water; at 110.0℃; for 2.0h;
A mixture of <strong>[55686-94-7]2-chloro-7-nitroquinoxaline</strong> (Combi-Blocks Catalog, No. QB-1085) (10 g, 48 mmol), XPhos Pd G2 (3.6 g, 4.8 mmol), and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (12 g, 57 mmol) in 1,4-dioxane (220 mL) and water (22 mL) was purged with nitrogen and stirred at 110 C. for 2 h. The reaction mixture was then cooled to room temperature, and filtered through a Celite plug with EtOAc. The volatiles were removed under reduced pressure and the crude material was taken forward without additional purification. LCMS calculated for C12H10N5O2 (M+H)+: m/z=256.1; Found: 256.1.