Reaktionsgleichung
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.[NH:12]1[C:20]2[C:15](=[CH:16][C:17]([S:21](Cl)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[CH:14]=[N:13]1.O>N1C=CC=CC=1>[OH:10][B:7]1[C:6]2[CH:11]=[C:2]([NH:1][S:21]([C:17]3[CH:16]=[C:15]4[C:20](=[CH:19][CH:18]=3)[NH:12][N:13]=[CH:14]4)(=[O:23])=[O:22])[CH:3]=[CH:4][C:5]=2[CH2:9][O:8]1Komponenten
Versuchsvorschrift
To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (0.385 g, 2.07 mmol) in anhydrous pyridine (30 mL) at 5° C. was added 1H-indazole-5-sulfonyl chloride (0.45 g, 2.07 mmol) and the resulting orange solution stirred at room temperature for 0.5 h. The reaction was warmed to 50° C. for 2 h and then the pyridine was removed under reduced pressure to afford a sticky residue. This was treated with water (40 mL) and sonicated for 5 h at 70° C. The fine precipitate that formed was collected by filtration, washed with water and dried in vacuo generating 0.402 g (59%) of the title compound as a yellowish orange solid. mp 222° C.; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.21 (s, 1H), 9.19 (s, 1H), 8.24 (s, 2H), 7.67 (s, 2H), 7.48 (d, J=1.2 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.17 (dd, J=8.2, 2.0 Hz, 1H), 4.84 (s, 2H); MS (ESI) m/z=330 (M+1, positive); HPLC purity: 97.30% (MaxPlot 200-400 nm), 97.30% (220 nm).
Aufarbeitung
- temperatureThe reaction was warmed to 50° C. for 2 h
- customthe pyridine was removed under reduced pressure
- customto afford a sticky residue
- customsonicated for 5 h at 70° C
- customThe fine precipitate that formed
- filtrationwas collected by filtration
- washwashed with water
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-6352720336c64614956846288d2c80b6
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08461134B2
Verknüpfte Notizen
Wird geladen…