Tris(furan-2-yl)phosphane → HCID 23077584, compound

HRID 1349495Notes

Reaction equation

HRID 1349495 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:30])[C:11](Br)=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[S:47]1[CH:51]=[CH:50][N:49]=[C:48]1[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[C:10](=[O:30])[C:11]([C:48]2[S:47][CH:51]=[CH:50][N:49]=2)=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 23077618HCID 23077618, compound

Product 1

HCID 23077584HCID 23077584, compound

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 9-benzyloxy-7-bromo-2-(3,4-dichlorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (150 mg) in dioxane (5 ml) were added tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (63 mg), tri-2-furylphosphine (57 mg) and (2-thiazolyl)tributyltin (0.285 ml) under an argon stream and a microwave at 80 W was irradiated under sealing for 1 hr. The obtained reaction mixture was concentrated, and then purified by silica gel column chromatography (chloroform:methanol=40:1) to give 9-benzyloxy-2-(3,4-dichlorobenzyl)-7-(thiazol-2-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (95 mg).

Workup

  1. customa microwave at 80 W was irradiated
  2. customThe obtained reaction mixture
  3. concentrationwas concentrated
  4. custompurified by silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-e8a389388c08435ba44723af7f147eb3
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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