Tetrahydrofuran → (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone

HRID 1778301Notes

Reaction equation

CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[C:9]2/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5].Cl[C:26]1[CH:31]=[CH:30][C:29]([Mg]Br)=[CH:28][CH:27]=1.C1C[O:37][CH2:36]C1>C(Cl)Cl.O>[CH3:36][O:37][C:26]1[CH:31]=[CH:30][C:29]([C:4]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][CH:10]=[C:9]3/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:5])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide (150 mg, 0.47 mmol) in anhydrous THF (2 mL) was dropwise added dropwise (4-chlorophenyl)magnesium bromide (0.5 M, 1.23 mL, 0.61 mmol) at 0° C. under N2 and the resulting reaction mixture was stirred at 0° C. for 3 hr. The reaction was diluted with CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organics were concentrated and purified by chromatography (15-20% EtOAc/hexanes) to yield (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)methanone. (ES, m/z) 366.0 [M+H]+

Workup

customthe resulting reaction mixture
extractionThe aqueous layer was extracted with CH2Cl2
concentrationthe combined organics were concentrated
custompurified by chromatography (15-20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-f32d476cf65b469093d52d3fb152349e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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