Dimethylformamide → HCID 86673791, compound

Temperature

0 °C

To a solution of oxalyl chloride (1.22 mL, 14.1 mmol) in dry CH2Cl2 (20 mL) was added at 0° C. under nitrogen a solution of dry DMF (1.3 mL) in dry CH2Cl2 (20 mL). The mixture was stirred at 0° C. for 30 min and a solution of 5-allyloxy-1H-indole (1.25 g, 7.22 mmol) in CH2Cl2 (10 mL) was added. The resulting solution was allowed to reach RT and stirred for 4 h. The solvent was concentrated and the residue dissolved in THF (35 mL) and 20% aqueous ammonium acetate (48 mL) and heated at reflux for 30 min, cooled, treated with an aqueous saturated solution of NaHCO3, and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude solid was taken up in CH2Cl2 and filtered-off to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:2)=0.56; MS (LC/MS): 202.0 [M+H]+, 224.1 [M+Na]+, 200.1 [M−H]−, 159.1 [M−H-allyl]−; tR (HPLC conditions a): 2.89 min.

1. customto reach RT
2. stirringstirred for 4 h
3. concentrationThe solvent was concentrated
4. dissolutionthe residue dissolved in THF (35 mL)
5. temperature20% aqueous ammonium acetate (48 mL) and heated
6. temperatureat reflux for 30 min
7. temperaturecooled
8. additiontreated with an aqueous saturated solution of NaHCO3
9. extractionextracted twice with EtOAc
10. dry with materialThe combined organic layers were dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-df73f8d0e14b4c89bd483ab7fff0eb74

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085555B2