Hydrochloric Acid → HCID 84740169, compound

HCl (g) was bubbled through a solution of (4,6-dimethyl-1H-indol-3-yl)acetonitrile from Step B (83.0 mg, 0.450 mmol) in MeOH (5 mL). The reaction mixture was stirred for 30 min, then H2O (1 mL) was added and stirring was continued for 2 h. The MeOH was removed under vacuum and the reaction mixture was extracted with EtOAc (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was dissolved in MeOH (2 mL) containing a drop of conc. H2SO4 and the resulting mixture was stirred for 16 h. The reaction mixture was partitioned between EtOAc (10 mL) and saturated NaCl (5 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude product by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 80:20, gave the title compound. MS: m/z=218 (M+1).

1. stirringstirring
2. waitwas continued for 2 h
3. customThe MeOH was removed under vacuum
4. extractionthe reaction mixture was extracted with EtOAc (5 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe crude product was dissolved in MeOH (2 mL)
9. additioncontaining a drop of conc. H2SO4
10. stirringthe resulting mixture was stirred for 16 h
11. customThe reaction mixture was partitioned between EtOAc (10 mL) and saturated NaCl (5 mL)
12. customThe layers were separated
13. dry with materialthe organic layer was dried over Na2SO4
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customPurification of the crude product by silica gel chromatography
17. washeluting with a gradient of hexane

ORD record

ord-8bb5c1ea865f4c22acff4d5204af411d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173655B2