Stannane, tributyl(1-ethoxyethenyl)- → HCID 89782044, compound

HRID 1055990Notes

Reaction equation

HRID 1055990 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O: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>C1(C)C=CC=CC=1.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[O:12]([C:9]1[CH:8]=[N:7][C:6]2[C:11]([N:10]=1)=[C:2]([C:24](=[O:26])[CH3:25])[CH:3]=[CH:4][CH:5]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 89782156HCID 89782156, compound

Product 1

HCID 89782044HCID 89782044, compound

Reagents, catalysts & solvents 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 1140TolueneSolvent

Procedure

A solution of 8-chloro-2-phenoxyquinoxaline (253 mg, 0.986 mmol), tributyl(1-ethoxyvinyl)stannane (499 μl, 1.478 mmol, Aldrich), and PdCl2(Amphos)2 (34.9 mg, 0.049 mmol) in toluene (9.9 ml) was stirred at 110° C. in a sealed tube for 16 h. Purification by silica gel (100% hexanes to 10% EtOAc/hexanes) provided 1-(3-phenoxyquinoxalin-5-yl)ethanone as a white solid. MS (ESI, pos. ion) m/z: 365.2 (M+1).

Workup

  1. customPurification by silica gel (100% hexanes to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-39d0fbf97ca74de5bb7120d39aa74967
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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