Dimethylformamide dimethyl acetal → 6-bromo-N-methylisoquinolin-3-amine

Temperature

110 °C

To a solution of 6-bromoisoquinolin-3-amine (50.0 mg, 2.6 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethylacetal (2 mL). The reaction vessel was sealed and heated in a Biotage Smith Synthesizer microwave to 110° C. for 20 minutes. Sodium triacetoxyborohydride (59 mg, 0.28 mmol) was then added to the reaction mixture. The vial was resealed and heated again to 110° C. on a Biotage Smith Synthesizer microwave for 10 minutes. The reaction was concentrated. The residue was dissolved in ethyl acetate (50 mL) and washed with brine (2×20 mL). The organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound (23 mg, 43%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.76 (s, 1H), 7.74 (s, 1H), 7.61 (d, 1H), 7.28 (d, 1H), 6.40 (s, 1H), 5.09-5.07 (m, 1H), 2.97 (s, 3H).

1. customThe reaction vessel was sealed
2. temperatureheated again to 110° C. on a Biotage Smith Synthesizer microwave for 10 minutes
3. concentrationThe reaction was concentrated
4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
5. washwashed with brine (2×20 mL)
6. dry with materialThe organics were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by flash column chromatography

ORD record

ord-62757f9dbbc84a259faa25cf267a7d40

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859773B2