Triphenylphosphine → HCID 17962887, compound

HRID 2382275Notes

Reaction equation

HRID 2382275 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:25])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=3Br)=[CH:11][CH:12]=2)[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH3:26])[CH2:6][C:5]1([CH3:34])[CH3:33])(=[O:3])[CH3:2].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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:25])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:11][CH:12]=2)[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH3:26])[CH2:6][C:5]1([CH3:34])[CH3:33])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 17962898HCID 17962898, compound

Product 1

HCID 17962887HCID 17962887, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

Suzuki cross-coupling of 1-acetyl-4-phenyl-6-(2-bromo-5-methoxybenzoyl)amino-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (30 mg), benzeneboronic acid (25 mg), cesium fluoride (21 mg), triphenylphosphine (7.0 mg) and tris(dibenzylideneacetone)dipalladium(0) (6.0 mg) in dimethoxyethane/ethanol 4:1 (v/v) (5 ml) was performed according to the method described in example 13.

Sources & evidence

ORD record
ord-0642615987b844dc968203b69e4ef2f0
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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