反应详情

A side-arm tube under a nitrogen atmosphere is charged with 1-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde (100 mg, 0.321 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (20 mg, 0.032 mmol) and sodium tert-butylate (46 mg, 0.479 mmol). To this is added toluene (3.0 mL), a solution of 2-methylaziridine (37 mg, 0.678 mmol) in toluene (1.0 mL) and the resulting mixture is stirred overnight at 80° C. The reaction is cooled, water added and the mixture is extracted with ethyl acetate. The combined ethyl acetate layer are washed with water, with brine, dried over sodium sulfate, filtered and the solvent concentrated to give an oil that is purified by chromatography eluting with heptane-5 to 30% ethyl acetate. Product containing fractions are combined and concentrated to afford 1-(4-tert-butyl-phenyl)-2-(2-methyl-aziridin-1-yl)-1H-indole-3-carboxaldehyde (70 mg, 66% yield) as a yellow solid. TLC (heptane-30% ethyl acetate/) Rf 0.20; ESI/MS 333 (M+H); RT 4.15 min; NMR 10.16 (1H, s); 8.08 (1H, d, J=6 Hz); 7.70 (2H, d, J=9 Hz); 7.49 (2H, d, 9 Hz); 7.21 (2H, m); 6.91 (1H, d, J=9 Hz); 2.43 (2H, m); 2.28 (1H, d); 1.38 (9H, s); 0.79 (3H, d, J=6 Hz).

1. temperatureThe reaction is cooled
2. extractionthe mixture is extracted with ethyl acetate
3. washThe combined ethyl acetate layer are washed with water, with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationthe solvent concentrated
7. customto give an oil that
8. customis purified by chromatography
9. washeluting with heptane-5 to 30% ethyl acetate
10. additionProduct containing fractions
11. concentrationconcentrated