(3-Ethylphenyl)boronic acid → Quinuclidin-3-yl3'-ethylbiphenyl-3-ylcarbamate

HRID 2281256Notes

Reaction equation

HRID 2281256 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.[CH2:20]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)[CH3:21]>>[CH2:20]([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)[CH3:21]

Participants

3

Reactant 2

HCID 16427138(3-Ethylphenyl)boronic acidHCID 54521110Quinuclidin-3-yl3-bromophenylcarbamate

Product 1

HCID 90386038Quinuclidin-3-yl3'-ethylbiphenyl-3-ylcarbamateYield 56%

Procedure

Using general procedure E, quinuclidin-3-yl 3-bromophenylcarbamate, 3-ethylphenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (78 mg, 56%). 1H NMR (500 MHz, CDCl3) δ 7.64 (br s, 1H), 7.43-7.27 (m, 6H), 7.24 (br s, 1H), 7.18 (d, J=8.0 Hz, 1H), 4.85 (m, 1H), 3.30 (m, 1H), 2.99-2.73 (m, 5H), 2.70 (q, J=7.5 Hz, 2H), 2.12 (m, 1H), 1.92-1.84 (m, 1H), 1.75-1.67 (m, 1H), 1.62-1.55 (m, 1H), 1.48-1.38 (m, 1H), 1.27 (t, J=7.5 Hz, 3H) ppm. 13C NMR (125 MHz, CDCl3) δ 153.5, 144.8, 142.4, 140.8, 138.4, 129.4, 128.8, 127.1, 126.8, 124.6, 122.3, 117.4, 72.1, 55.4, 47.4, 46.5, 29.0, 25.4, 24.5, 19.5, 15.7 ppm. Purity: >98% LCMS (214 nm & 254 nm); retention time 1.66 min: (M+1) 351.

Sources & evidence

ORD record
ord-5ceb2e582fe3424d9b17b88e12f3226c
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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