Diisopropylethylamine → cis-3-Benzyl-1-(4-methoxyphenylsulfonyl)-4-phenyl-3,4-dihydropyridin-2(1h)-one

HRID 1886850Notes

Reaction equation

Cl[CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:3]=[O:4].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]=[CH:24]/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>>[CH2:5]([C@H:2]1[C@@H:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:24][N:23]([S:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)(=[O:22])=[O:21])[C:3]1=[O:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 110628112-Chloro-3-phenylpropanal

HCID 68489412trans-N-(4-methoxybenzenesulfonyl)-3-phenylprop-2-en-1-imine

Product 1

HCID 59445869cis-3-Benzyl-1-(4-methoxyphenylsulfonyl)-4-phenyl-3,4-dihydropyridin-2(1h)-oneYield 40%

Procedure

The title compound was prepared according to the general procedure from 2-chloro-3-phenylpropanal and trans-N-(4-methoxybenzenesulfonyl)-3-phenyprop-2-ene-1-imine using 10 mol % 7 and 1.5 equiv DIPEA in 40% yield. 1H NMR (400 MHz, CDCl3) δ 8.02 (dd, 2H, J=7.0, 2.1 Hz), 7.24-7.10 (m, 4H), 7.09-6.94 (m, 7H), 6.47 (dd, 2H, J=8.0, 1.0 Hz), 5.48 (dd, 1H, J=8.0, 6.3 Hz), 3.90 (s, 3H), 3.33-3.30 (m, 1H), 3.27-3.21 (m, 1H), 3.15 (dd, 1H, J=14.6, 4.3 Hz), 2.10 (dd, 1H, J=14.6, 9.0 Hz); 13C NMR (100 MHz, CDCl3) δ 170.2, 164.3, 138.8, 137.4, 131.5, 129.2, 129.1, 128.8, 128.7, 128.2, 127.7, 126.6, 124.1, 114.4, 114.3, 56.0, 48.9, 41.1, 31.5; IR (thin film) ν 3062, 3029, 2926, 1721, 1594, 1496, 1362, 1263, 1167, 1091, 1027 cm−1; HRMS (ESI) calcd for C25H23NO4S [M+Na]+ XX, found XX.

Sources & evidence

ORD record: ord-3f92fb83c1ed49c680cb3ba75cb41905
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501658B2

Reaction notes

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