Phenylboronic Acid → Quinuclidin-3-yl biphenyl-2-ylcarbamate

HRID 2274919Notes

Reaction equation

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

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 68327765Quinuclidin-3-yl2-bromophenylcarbamate

Product 1

HCID 10496082Quinuclidin-3-yl biphenyl-2-ylcarbamateYield 87%

Procedure

Using general procedure E, quinuclidin-3-yl2-bromophenylcarbamate (130 mg, 0.400 mmol), phenylboronic acid (96 mg, 0.8 mmol) and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (112 mg, 87%). 1H NMR (400 MHz, CDCl3) δ 8.07 (br s, 1H), 7.55-7.33 (m, 6H), 7.25-7.21 (dd, J=7.6 & 1.6 Hz, 1H), 7.43 (td, J=8.0, 1.2 Hz, 1H), 6.65 (br s, 1H), 4.78 (m, 1H), 3.24 (m, 1H), 2.90-2.68 (m, 5H), 2.04 (m, 1H), 1.80-1.62 (m, 2H), 1.61-1.50 (m, 1H), 1.41-1.30 (m, 1H) ppm. 13C NMR (100 MHz, CDCl3) δ 151.2, 135.9, 132.5, 129.5, 128.0, 127.0, 126.9, 126.2, 125.7, 121.4, 117.9, 69.9, 53.1, 45.1, 44.3, 23.1, 22.3, 17.2 ppm. Purity: 100% LCMS (214 nm & 254 nm); retention time 1.47 min; (M+1) 323.

Sources & evidence

ORD record: ord-8deaec6a72324346a47d2a882b29fd4e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126993B2

Reaction notes

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