Ethanol → HCID 57742092, compound

To a solution of 3-isopropylbenzofuran-2-carbaldehyde (250 mg, 1.33 mmol) in anhydrous methanol (8 mL) is added a solution of n-methylamine in ethanol (0.281 mL, 5.32 mmol) and the reaction is stirred at room temperature overnight under an atmosphere of argon. The solution is then concentrated, and re-solvated in methanol (8 mL) and cooled in an ice bath. Sodium borohydride (0.152 g, 4 mmol) was added portion wise and the reaction was stirred at room temperature under argon for 6 h. The solution is concentrated, and re-solvated in 1.3N NaOH (5 mL) and ether (5 mL) and stirred for 1 h. The ether layer was collected. The aqueous layer was washed with ether (2×10 mL), and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by chromatography (silica gel, 9:1 DCM:MeOH) yielded the title compound as a yellow oil (228 mg, 85%): 1H NMR (400 MHz, DMSO-d6) δ 7.70 (d, J=4.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.25-7.16 (m, 2H), 3.75 (s, 2H), 3.15-3.22 (m, 1H), 2.25 (s, 3H), 1.36-1.34 (2s, 6H).

1. concentrationThe solution is then concentrated
2. temperaturere-solvated in methanol (8 mL) and cooled in an ice bath
3. stirringthe reaction was stirred at room temperature under argon for 6 h
4. concentrationThe solution is concentrated
5. stirringre-solvated in 1.3N NaOH (5 mL) and ether (5 mL) and stirred for 1 h
6. customThe ether layer was collected
7. washThe aqueous layer was washed with ether (2×10 mL)
8. dry with materialthe combined organic layers were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification by chromatography (silica gel, 9:1 DCM:MeOH)

ORD record

ord-0ab06170013d4ff9937766cc33d7b812

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2