(Naphthalen-2-yl)boronic acid → 4-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole

HRID 913055Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1B(O)O>C1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[CH:23]1[C:24]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:22]=1[C:2]1[N:3]=[CH:4][N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of E1 (1.0 eq.) in benzene (0.1 M solution), 2-naphthylboronic acid (1.5 eq.) and sat. aq. Na2CO3 solution under argon was added PdCl2((PPh)3)2. The mixture was stirred for 72 hr at 60° C., then cooled and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether to obtain E2 as yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.31 (1H, s), 7.88-7.70 (5H, m), 7.48-7.39 (3H, m), 5.28 (2H, s), 3.54 (2H, t, J=8.2 Hz), 0.94 (2H, t, J=8.2 Hz), 0.00 (9H, s). MS (ES) C19H24N2OSi requires: 324, found: 325 (M+H)+.

Workup

temperaturecooled
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether

Sources & evidence

ORD record: ord-a82647610e064d4295f3ad5357489492
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026265B2

Reaction notes

Loading…