2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) → Quinuclidin-3-yl2'-ethylbiphenyl-3-ylcarbamate

HRID 2281254Notes

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

Participants

Reactant 2

HCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

HCID 54521110Quinuclidin-3-yl3-bromophenylcarbamate

Product 1

HCID 68327795Quinuclidin-3-yl2'-ethylbiphenyl-3-ylcarbamateYield 78%

Procedure

Using general procedure E, quinuclidin-3-yl 3-bromophenylcarbamate, 2-ethylphenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title v compound as a white solid (110 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.42-7.28 (m, 5H), 7.25-7.16 (m, 2H), 7.03-7.00 (m, 1H), 6.88 (br s, 1H), 4.83 (m, 1H), 3.27 (m, 1H), 2.98-2.70 (m, 5H), 2.61 (q, J=7.6 Hz, 2H), 2.08 (m, 1H), 1.92-1.80 (m, 1H), 1.75-1.65 (m, 1H), 1.63-1.55 (m, 1H), 1.46-1.37 (m, 1H), 1.10 (t, J=7.6 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3) δ 152.1, 141.7, 140.4, 139.9, 136.4, 128.6, 127.5, 127.4, 126.4, 124.3, 123.2, 118.4, 115.9, 71.0, 54.3, 46.2, 45.3, 25.0, 24.2, 23.4, 18.3, 14.5 ppm. Purity: 100% LCMS (214 nm & 254 nm); retention time 1.61 min; (M+1) 351.

Sources & evidence

ORD record: ord-785324d0f6504bf2abdec7e5ef5cec00
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139580B2

Reaction notes

Loading…