1,2,3,4-Tetrahydroisoquinoline → 2-(6-Fluoro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 1445088Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.F[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]([F:21])[N:13]=1>C1(C)C=CC=CC=1>[F:21][C:14]1[N:13]=[C:12]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1,2,3,4-Tetrahydroisoquinoline (34.8 ml, 0.28 mol) was added to a solution of 2,6-difluoro-3-nitropyridine (44.55 g, 0.28 mol) prepared in Step 1 in toluene (200 ml). The reaction mixture was stirred overnight at 60° C. and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=1/4, v/v) to give 5.38 g of the titled compound as yellow solid.

Workup

concentrationconcentrated under reduced pressure
customThe resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=1/4, v/v)

Sources & evidence

ORD record: ord-47c52839b1d84a66ab77b31e475f07e9
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662832B2

Reaction notes

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