Cesium fluoride → HCID 89781962, compound

HRID 1055997Notes

Reaction equation

HRID 1055997 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:8]=[N:7]2.C([Sn](CCCC)(CCCC)[C:24]([O:26]CC)=[CH2:25])CCC.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F-].[Cs+]>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.[Pd].[Pd].[Cu]I>[C:13]1([NH:12][C:9]2[CH:8]=[N:7][C:6]3[C:11]([N:10]=2)=[C:2]([C:24](=[O:26])[CH3:25])[CH:3]=[CH:4][CH:5]=3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 89782295HCID 89782295, compound

Product 1

HCID 89781962HCID 89781962, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 8-chloro-N-phenylquinoxalin-2-amine (0.65 g, 2.54 mmol), tributyl(1-ethoxyvinyl)stannane (1.288 ml, 3.81 mmol, Aldrich), Pd2(dba)3 (0.582 g, 0.636 mmol), XPhos (Strem, Newburyport, Mass.; 0.303 g, 0.636 mmol), copper(I) iodide (0.097 g, 0.508 mmol), and cesium fluoride (0.772 g, 5.08 mmol) in dioxane (12.71 ml) was heated in a microwave (Biotage Initiator) for 20 min at 160° C. Purification by silica gel (100% hexanes to 30% EtOAc/hexanes) provided 1-(3-(phenylamino)quinoxalin-5-yl)ethanone (180b, 78% yield) as a yellow oil. MS (ESI, pos. ion) m/z: 264.2 (M+1).

Workup

  1. customPurification by silica gel (100% hexanes to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4e5e0f9ddf27428c9c008e7f20b42f3a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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