Dimethylformamide → HCID 86698654, compound

Phosphorous oxychloride (84.3 mg, 0.54 mmol) was added to DMF (1 mL) at 0° C. and the reaction mixture was stirred for 15 minutes. To this solution was added 5-(4-methoxy-phenyl)-1H-indole-6-carbonitrile (150.0 mg, 0.60 mmol) in DMF (1 mL) and the reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, treated with additional phosphorous oxychloride (84.3 mg, 0.54 mmol) and stirred at 45° C. for an additional hour. The reaction mixture was cooled to room temperature, and quenched with water (10 mL). The solution was concentrated in vacuo, and the residue was partitioned between water (10 mL) and EtOAc (10 mL). The layers were separated and the organic layer was concentrated in vacuo. The crude material was slurried in CH2Cl2, and the resulting solid was filtered and air dried to give the title compound (85 mg, 51% yield). MS (ES−) 275.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 12.63 (br. s., 1 H), 10.00 (s, 1 H), 8.58 (d, J=3.12 Hz, 1 H), 8.17 (s, 1 H), 8.10 (s, 1 H), 7.51 (d, J=8.59 Hz, 2 H), 7.09 (d, J=8.80 Hz, 2 H), 3.83 (s, 3 H).

1. stirringthe reaction mixture was stirred at 40° C. for 1 hour
2. stirringstirred at 45° C. for an additional hour
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched with water (10 mL)
5. concentrationThe solution was concentrated in vacuo
6. customthe residue was partitioned between water (10 mL) and EtOAc (10 mL)
7. customThe layers were separated
8. concentrationthe organic layer was concentrated in vacuo
9. filtrationthe resulting solid was filtered
10. customair dried

ORD record

ord-f8f2be615aac49099782b099f63beb4a

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2