(3-Methoxyphenyl)boronic acid → Quinuclidin-3-yl3'-methoxybiphenyl-2-ylcarbamate

HRID 2281260Notes

Reaction equation

HRID 2281260 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:19])[O:10][CH:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]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]=[CH:4][C:3]=2[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:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 68327765Quinuclidin-3-yl2-bromophenylcarbamate

Product 1

HCID 68328075Quinuclidin-3-yl3'-methoxybiphenyl-2-ylcarbamateYield 85%

Procedure

Using general procedure E, quinuclidin-3-yl 2-bromophenylcarbamate, 3-methoxyphenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (120 mg, 85%). 1H NMR (500 MHz, CDCl3) δ 8.08 (br s, 1H), 7.40 (t, J=7.5 Hz, 1H), 7.36 (t, J=7.5 Hz, 1H), 7.23 (dd, J=7.5, 1.5 Hz, 1H), 7.13 (td, J=7.5, 1.5 Hz, 1H), 6.96 (dd, J=8.0, 2.0 Hz, 2H), 6.91 (t, J=1.5 Hz, 1H), 6.73 (br s, 1H), 4.79 (m, 1H), 3.84 (s, 3H), 3.24 (m, 1H), 2.90-2.70 (m, 5H), 2.05 (m, 1H), 1.80-1.70 (m, 2H), 1.62-1.52 (m, 1H), 1.41-1.32 (m, 1H) ppm. 13C NMR (125 MHz, CDCl3) δ 160.1, 153.4, 139.5, 134.7, 131.5, 130.1, 130.1, 128.5, 123.5, 121.4, 119.9, 114.7, 113.6, 72.1, 55.3, 55.3, 47.3, 46.5, 25.3, 24.5, 19.4 ppm. Purity: >98% LCMS (214 nm & 254 nm); retention time 1.48 min; (M+1) 353

Sources & evidence

ORD record
ord-e141b20de2a64b858d65077fcb54b548
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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