[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:17].C(N([CH:24]([CH3:26])[CH3:25])CC)(C)C.[C:27](Cl)(Cl)=[O:28].C[N:32](C)[CH2:33][C:34]#[C:35]CC.Cl[CH2:40]Cl>C1(C)C=CC=CC=1>[CH3:40][C:24]([CH3:25])([CH3:26])[C:35]#[C:34][CH2:33][NH:32][C:27]([NH:17][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)[C:2]=1[CH3:1])=[O:28]To a cooled solution of 2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (29 mg, 0.13 mmol) in 2.4 mL of dichloromethane were added 0.11 mL (0.66 mmol) of diisopropylethylamine and 78 uL of a 20% solution of phosgene in toluene at 0 C. The reaction mixture was stirred at 0 C for 20 minutes and transferred into a flask containing 140 mg (18% pure, 0.17 mmol) of dimethyl-pent-2-ynylamine. The reaction mixture was stirred at RT for 18 hour then applied to column chromatography without workup. Chromatography (0->50% in hexanes/ethyl acetate in 30 minutes) gave 27 mg (73 umol, 60%) of the title compound.
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