(3-Methoxyphenyl)boronic acid → Quinuclidin-3-yl3'-methoxybiphenyl-3-ylcarbamate

HRID 2281255Notes

Reaction equation

HRID 2281255 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:19])[O:10][CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9](=[O:19])[O:10][CH:11]3[CH:16]4[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]4)[CH2:12]3)[CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 54521110Quinuclidin-3-yl3-bromophenylcarbamate

Product 1

HCID 68327822Quinuclidin-3-yl3'-methoxybiphenyl-3-ylcarbamateYield 71%

Procedure

Using general procedure E, quinuclidin-3-yl 3-bromophenylcarbamate, 3-methoxyphenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (100 mg, 71%). 1H NMR (500 MHz, CDCl3) δ 7.63 (br s, 1H), 7.40-7.27 (m, 4H), 7.17 (d, J=8.0 Hz, 1H), 7.11 (m, 1H), 7.07 (br s, 1H), 6.89 (dd, J=8.0, 2.0 Hz, 1H), 4.85 (m, 1H), 3.85 (s, 3H), 3.30 (m, 1H), 2.99-2.70 (m, 5H), 2.12 (m, 1H), 1.92-1.84 (m, 1H), 1.75-1.68 (m, 1H), 1.62-1.55 (m, 1H), 1.48-1.40 (m, 1H) ppm. 13C NMR (125 MHz, CDCl3) δ 159.9, 153.4, 142.3, 142.1, 138.4, 129.8, 129.4, 122.3, 119.7, 117.7, 112.9, 112.8, 72.0, 55.4, 55.3, 47.4, 46.5, 25.4, 24.5, 19.5 ppm. Purity: >97% LCMS (214 nm & 254 nm); retention time 1.52 min; (M+1) 353

Sources & evidence

ORD record
ord-758fb89bb79c49eab23e125017c85fd9
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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