1-Bromo-4-fluorobenzene → methyl 8-[(2R)-(1-(4-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 41210Notes

Reaction equation

HRID 41210 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][C:31]([F:34])=[CH:30][CH:29]=1>>[F:34][C:31]1[CH:32]=[CH:33][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:29][CH:30]=1

Participants

3

Reactant 2

HCID 99931-Bromo-4-fluorobenzeneHCID 86672411methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate

Product 1

HCID 86672433methyl 8-[(2R)-(1-(4-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylateYield 15%

Procedure

Methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (130 mg, 0.36 mmol) was reacted with 1-bromo-4-fluorobenzene (0.239 ml, 2.18 mmol) to afford methyl 8-[(2R)-(1-(4-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (enantiomer 2, 24 mg, 15%) as a beige solid. Mass Spectrum: m/z [M+H]+=453.

Sources & evidence

ORD record
ord-d7eb541d698149f8961e513e82cfcd62
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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