3-Bromoanisole → methyl 8-[(2R)-(1-(3-methoxyphenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 41198Notes

Reaction equation

HRID 41198 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:14]([C:15](=[O:17])[CH:16]=2)=[CH:13][C:12]([C:18]([O:20][CH3:21])=[O:19])=[CH:11][C:10]=3[C@H:22]2[CH2:26][CH2:25][CH2:24][NH:23]2)[CH2:3][CH2:2]1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1>>[CH3:35][O:34][C:30]1[CH:29]=[C:28]([N:23]2[CH2:24][CH2:25][CH2:26][C@@H:22]2[C:10]2[CH:11]=[C:12]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=[C:14]3[C:9]=2[O:8][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][C:15]3=[O:17])[CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 169713-BromoanisoleHCID 86672411methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate

Product 1

HCID 86672422methyl 8-[(2R)-(1-(3-methoxyphenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylateYield 56%

Procedure

Methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate, preparation described in Example 1.03b, 125 mg, 0.35 mmol) was reacted with 1-bromo-3-methoxybenzene (0.049 ml, 0.38 mmol) using a procedure similar to that described in Example 1.0 to afford methyl 8-[(2R)-(1-(3-methoxyphenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (90 mg, 56%) as a yellow gum. Mass Spectrum: m/z [M+H]+=465.

Sources & evidence

ORD record
ord-feef3925f43e4c0184e2845e238e1936
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

Loading…