Tetrahydrofuran → Methyl 4'-[[2-butyl-4-quinolinyl]-methyl]1,1'-biphenyl-2-carboxylate

HRID 398989Notes

Reaction equation

HRID 398989 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:3]=1.[Br-].[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([Zn]C)=[CH:29][CH:28]=1)=[O:20].O1CCC[CH2:36]1>[Zn]>[CH2:12]([C:4]1[CH:3]=[C:2]([CH2:36][C:30]2[CH:31]=[CH:32][C:27]([C:22]3[C:21]([C:19]([O:18][CH3:17])=[O:20])=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:28][CH:29]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 110422352-Butyl-4-chloroquinolineHCID 178497618HCID 178497618, compound

Product 1

HCID 19595345Methyl 4'-[[2-butyl-4-quinolinyl]-methyl]1,1'-biphenyl-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Using the procedure of Step G of Example 1, 500 mg of 2-butyl-4-chloro quinoline of Step D were introduced into a previously prepared solution of 475 mg of electrolytic zinc, 275 mg of tetrakistriphenyl-phosphine palladium and 2.075 g of [[2'-(methoxycarbonyl)(1,1'-biphenyl)-4-yl]-methyl zinc bromide prepared as in Example 1 in 13 ml of tetrahydrofuran. After chromatographing on silica (eluant:choloroform-hexane-ethyl acetate 100-100-10), 621 mg of the expected product were obtained.

Sources & evidence

ORD record
ord-f2fda2e088de4fbcbcf533c896ea64ff
Source dataset
uspto-grants-1998_10
Patent number
US05817674

Reaction notes

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