[CH3:1][O:2][C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:24])[O:20][CH:21]([CH3:23])[CH3:22].[H-].[Na+].I[CH3:28].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:14])([CH3:15])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:5][C:4]=1[N:18]([CH3:28])[C:19](=[O:24])[O:20][CH:21]([CH3:22])[CH3:23]
To isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (0.298 mmol, 0.10 g) in tetrahydrofuran (1 ml) at room temperature were subsequently added sodium hydride (60% dispersion in mineral oil, 0.350 mmol, 0.014 g) and iodomethane (0.803 mmol, 0.05 ml). After 1 hour aqueous ammonium chloride solution was added and extracted with dichloromethane (three times). The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to yield isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl(methyl)carbamate (0.14 g) which was used without further purification.
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