Methanol → HCID 21950056, compound

To a solution of 1-[3-(tert-butyldimethylsilyloxy) propyl]-1H-indole (4.99 g, 17.2 mmol) in diethyl ether (20 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (9.5 mL, 19.0 mmol). The resulting solution was allowed to warm to room temperature. After 2 h, the solution was cooled to −78° C. To this solution was added a 25% (w/w) solution of sodium methoxide in methanol (8.7 mL, 38.0 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 3 h. The reaction was quenched with water (10 mL) and poured into EtOAc (100 mL). The aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with saturated aq NH4Cl (100 mL) and brine (100 mL), dried (MgSO4), filtered, and concentrated. Flash chromatography (SiO2, 20% to 80% EtOAc/hexanes) gave the title compound (3.24 g, 71%) as a white solid. 1H NMR (300 MHz, CDCl3) 8.42 (m, 2H), 7.47 (m, 1H), 7.36 (m, 2H), 4.38 (m, 2H), 3.94 (s, 3H), 3.67 (m, 2H), 2.25 (m, 2H), 1.50 (m, 1H). MS (atmospheric pressure chemical ionization, m/z) 262 (M++1).

1. temperaturethe solution was cooled to −78° C
2. temperatureto warm to room temperature
3. customThe reaction was quenched with water (10 mL)
4. additionpoured into EtOAc (100 mL)
5. extractionThe aqueous layer was extracted with EtOAc (20 mL)
6. washThe combined organic layers were washed with saturated aq NH4Cl (100 mL) and brine (100 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-4e307d12ad4241d58255988a9d093c0f

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109229B2