Dibutyltin dichloride → (4-Cyclopropylmethyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-methanone

HRID 1025819Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH2:15][CH2:14]1)=[O:12].[CH:28]1([CH:31]=O)[CH2:30][CH2:29]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>>[CH:28]1([CH2:31][N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]([C:11]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:2]=3[Cl:1])=[O:12])[CH2:14][CH2:15]2)[CH2:30][CH2:29]1

Participants

Reactant 4

HCID 12688Dibutyltin dichloride

HCID 12752Phenylsilane

HCID 123114Cyclopropanecarboxaldehyde

HCID 53311864[4-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone

Product 1

HCID 53311867(4-Cyclopropylmethyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-methanone

Procedure

The title compound was prepared in analogy to Example 5, from [4-(2,5-dichloro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone (Example 3), cyclopropanecarboxaldehyde (commercially available; CAS RN 1489-69-6), dibutyltin dichloride and phenylsilane. Light brown solid (53%). MS (ESI): m/z=454.109 [M+H]+.

Sources & evidence

ORD record: ord-f41dbc5df7d9417ead0ae5f7a8f50467
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729091B2

Reaction notes

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