Electric Literature of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .In analogy to intermediate 1A, 200 mg (0.87 mmol) 5-(trifluoromethoxy)-1 H-indole-2,3-dione was heated with 388 muL (4.33 mmol) 1,1,1 -trifluoroacetone, 53 mg (0.95 mmol) potassium hydroxide, 99 muL (1.73 mmol) acetic acid and 99 mg (1.21 mmol) sodium acetate in 2 mL water for 1 h at 120 C in the microwave to obtain 269 mg (0.83 mmol, 96%) of the desired title compound after aqueous work-up.1 H NMR (400 MHz, DMSO d6): delta (ppm) = 8.01 (dd, 1 H), 8.38 (s, 1 H), 8.44 (d, 1 H), 8.85 – 8.89 (m, 1 H), 14.57 (br. s. , 1 H).
The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem