2-Methoxyphenylboronic acid → Quinuclidin-3-yl2'-methoxybiphenyl-3-ylcarbamate

HRID 2281253Notes

Reaction equation

HRID 2281253 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:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O>>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[CH:7]=[CH:6][CH:5]=[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:3]=1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 54521110Quinuclidin-3-yl3-bromophenylcarbamate

Product 1

HCID 68327852Quinuclidin-3-yl2'-methoxybiphenyl-3-ylcarbamateYield 58%

Procedure

Using general procedure E, quinuclidin-3-yl 3-bromophenylcarbamate, 2-methoxy-phenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (75 mg, 58%). 1H NMR (500 MHz, CDCl3) δ 7.49 (br s, 1H), 7.41 (br s, 1H), 7.37-7.28 (m, 3H), 7.23 (d, J=7.5 Hz, 1H), 7.04-6.94 (m, 3H), 4.83 (m, 1H), 3.80 (s, 3H), 3.29 (m, 1H), 2.97-2.70 (m, 5H), 2.10 (m, 1H), 1.91-1.82 (m, 1H), 1.74-1.65 (m, 1H), 1.62-1.53 (m, 1H), 1.46-1.37 (m, 1H) ppm. 13C NMR (125 MHz, CDCl3) δ 156.4, 153.4, 139.4, 137.6, 130.9, 130.2, 128.8, 128.6, 124.8, 120.8, 119.9, 117.3, 111.2, 72.0, 55.6, 55.4, 47.4, 46.5, 25.4, 24.5, 19.5 ppm. Purity: >95% LCMS (214 nm & 254 nm); retention time 1.52 min; (M+1) 353.

Sources & evidence

ORD record
ord-61c571ac152f49a8bebb4853edf4b9da
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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