Phenylboronic Acid → N-(2-(biphenyl-4-yl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide

HRID 2281251Notes

Reaction equation

HRID 2281251 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:22])[CH2:13][CH:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:22])[CH2:13][CH:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 68327949N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide

Product 1

HCID 68327909N-(2-(biphenyl-4-yl)propan-2-yl)-2-(quinuclidin-3-yl)acetamideYield 32%

Procedure

Using general procedure E, N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide (200 mg, 0.550 mmol), phenylboronic acid (134 mg, 1.00 mmol) and [PdCl2(pddf)]CH2Cl2 gave the title compound as a viscous brown oil (58 mg, 32%). 1H NMR (500 MHz, CDCl3) δ 7.58-7.50 (m, 4H), 7.44-7.37 (m, 4H), 7.31 (t, J=7.0 Hz, 1H), 6.50 (s, 1H), 3.16 (m, 1H), 3.02 (m, 1H), 2.92-2.78 (m, 3H), 2.60 (m, 1H), 2.40-2.20 (m, 3H), 1.47-1.90 (m, 11H) ppm. 13C NMR (125 MHz, CDCl3) δ 170.5, 146.1, 140.7, 139.2, 128.8, 127.2, 127.0 125.2, 55.6, 53.1, 46.8, 46.2, 40.3, 31.7, 29.3, 29.2, 26.0, 24.4, 19.7 ppm. Purity: 100% LCMS (214 nm & 254 nm); retention time 1.55 min; (M+1) 363.

Sources & evidence

ORD record
ord-3aec2a0e9d924a4fae7029d1ea9d03e3
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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