Triphenylphosphine → HCID 17962894, compound

HRID 2382272Notes

Reaction equation

HRID 2382272 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH3:24])[CH2:6][C:5]1([CH3:32])[CH3:31])(=[O:3])[CH3:2].[Cl:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.[F-].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(COC)OC.C(O)C.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.[Pd].[Pd]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([C:37]4[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=4)=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH3:24])[CH2:6][C:5]1([CH3:32])[CH3:31])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 742994-Chlorophenylboronic acidHCID 17962904HCID 17962904, compound

Product 1

HCID 17962894HCID 17962894, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

A mixture of 1-acetyl-6-(4-iodobenzoyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (25 mg), 4-chlorobenzeneboronic acid (22 mg), cesium fluoride (14 mg), triphenylphosphine (5.0 mg) and tris(dibenzylideneacetone)dipalladium(0). (4.3 mg) in dimethoxyethane/ethanol 4:1 (5 ml) was stirred for 15 min. as nitrogen was bubbled through the solution. After 3 h. at 80° C. the reaction mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate and washed with 0.5 M HCl, water, 5% aq. NaHCO3, water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>0/1 (v/v) as eluent.

Workup

  1. customwas bubbled through the solution
  2. concentrationAfter 3 h. at 80° C. the reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with 0.5 M HCl, water, 5% aq. NaHCO3, water and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-04c47a8f25a041e581d2273d881f19e5
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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