Methylamine → 3,5-Dimethoxy-N-methylbenzenamine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Cl)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:12][NH2:13].CC([O-])(C)C.[Na+]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].CC(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)[NH:13][CH3:12]Participants
Procedure
Following general procedure A, a mixture of 3,5-dimethoxychlorobenzene (173 mg, 1.0 mmol), 2M methylamine (1 mL, 2.0 mmol), NaOt-Bu (120 mg, 1.2 mmol), BrettPhos precatalyst 10 (8 mg, 0.01 mmol), and t-BuOH (1 mL) was stirred at room temperature for 2 h. The crude product was purified via column chromatography (80:20 to 50:50 Hexanes/EtOAc gradient) to provide the title compound as a pale yellow liquid (150 mg, 90%). 1H NMR (400 MHz, CDCl3) δ: 5.89 (t, J=2.2 Hz, 1H), 5.80 (t, J=2.2 Hz, 2H), 3.76 (s, 7H), 2.81 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 161.9, 151.5, 91.4, 89.7, 55.3, 30.9 ppm. Brown, F. J.; Bernstein, P. R.; Cronk, L. A.; Dosset, D. L.; Hebbel, K. C.; Maduskuie, T. P.; Shapiro, H. S.; Vacek, E. P.; Yee, Y. K.; Willard, A. K.; Krell, R. D.; Snyder, D. W. J. Med. Chem. 1989, 32, 807.
Workup
- customThe crude product was purified via column chromatography (80:20 to 50:50 Hexanes/EtOAc gradient)
Sources & evidence
- ORD record
- ord-9e374ecc78214736a28dc87f908c13de
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858784B2
Reaction notes
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