Bromomethyl 4-methoxyphenyl ketone → 4-(4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

HRID 446822Notes

Reaction equation

HRID 446822 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:10]2[CH2:14][O:13][C:12](=[O:15])[C:11]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].BrCC(C1C=CC(OC)=CC=1)=O>>[CH3:9][O:8][C:7]1[CH:2]=[CH:3][C:4]([C:10]2[CH2:14][O:13][C:12](=[O:15])[C:11]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 583680064-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

Product 1

HCID 583679974-(4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

Procedure

Following the procedure for the preparation of 4-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one using 2-bromo-1-(4-methoxyphenyl)ethanone provided the title compound. 1H NMR (500 MHz, CDCl3): δ 8.86-8.78 (m, 2H), 8.21 (d, J=7.8 Hz, 1H), 8.08 (d, J=7.6 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.68-7.64 (m, 1H), 7.58-7.50 (m, 1H), 7.39 (d, J=7.2 Hz, 2H), 7.29-7.21 (m, 1H), 7.02 (d, J=7.4 Hz, 2H), 6.92 (d, J=7.4 Hz, 2H), 5.41 (s, 2H), 5.05 (s, 2H), 3.92 (s, 3H). MS: M+H: m/z=424.2; M+Na: m/z=446.1. HPLC: 90%, (Condition-C).

Sources & evidence

ORD record
ord-269d187758794c59a38cd892b21d227f
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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