(Pyrimidin-5-yl)boronic acid → Carbamic acid, N-[[3-(5-pyrimidinyl)phenyl]methyl]-, 1-azabicyclo[2.2.2]oct-3-yl ester

HRID 2274907Notes

Reaction equation

HRID 2274907 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7](=[O:17])[O:8][CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1.[N:21]1[CH:26]=[C:25](B(O)O)[CH:24]=[N:23][CH:22]=1>>[N:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=2)[CH2:5][NH:6][C:7](=[O:17])[O:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:24]=[N:23][CH:22]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 68328080HCID 68328080, compound

Product 1

HCID 90386033Carbamic acid, N-[[3-(5-pyrimidinyl)phenyl]methyl]-, 1-azabicyclo[2.2.2]oct-3-yl esterYield 54.2%

Procedure

Using general procedure E, quinuclidin-3-yl 3-bromobenzylcarbamate (203 mg, 0.600 mmol), pyrimidin-5-ylboronic acid (149 mg, 1.2 mmol) and [PdCl2(pddf)]CH2Cl2 gave the title compound as a viscous semi-solid (110 mg, 54%). 1H NMR (500 MHz, CDCl3) δ 9.20 (s, 1H), 8.94 (s, 2H), 7.51 (m, 3H), 7.40 (m, 1H), 5.62 (m, 1H), 4.81 (m, 1H), 4.50-4.40 (m, 2H), 3.30 (m, 1H), 2.97-2.65 (m, 5H), 2.12 (m, 1H), 1.92-1.82 (m, 1H), 1.79-1.69 (m, 1H), 1.65-1.56 (m, 1H), 1.50-1.42 (m, 1H) ppm. 13C NMR (125 MHz, CDCl3) δ 157.6, 156.2, 154.9, 140.1, 134.7, 134.1, 129.8, 128.2, 126.2, 70.9, 55.2, 47.2, 46.2, 44.8, 25.2, 23.8, 19.0 ppm. Purity: >95% LCMS (214 nm & 254 nm); retention time 1.22 min; (M+1) 339.

Sources & evidence

ORD record
ord-fc99d78808d54c3fa42239d92e477811
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

Loading…