Stannane, tributyl(1-ethoxyethenyl)- → HCID 66700086, compound

HRID 1747011Notes

Reaction equation

HRID 1747011 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[N:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9](Br)=[CH:8][CH:7]=3)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:22]([O:24][CH2:25][CH3:26])=[CH2:23])CCC>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:25]([O:24][C:22]([C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[N:5][C:6]3[C:11]([N:12]=2)=[CH:10][C:9]([C:22]([O:24][CH2:25][CH3:26])=[CH2:23])=[CH:8][CH:7]=3)[CH:3]=1)=[CH2:23])[CH3:26]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 12560083HCID 12560083, compound

Product 1

HCID 66700086HCID 66700086, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,7-dibromophenazine (13-2) (1.52 g, 4.50 mmol) in dry dioxane (75 mL) under N2 was added tributyl(1-ethoxyvinyl)stannane (3.34 ml, 9.89 mmol) and Pd(dppf)Cl2 (0.316 g, 0.450 mmol). The resultant mixture was heated at 100° C. for 4 h in a sealed tube. The crude reaction mixture was filtered through CELITE™545, and the volatiles were removed in vacuo. The crude brown solid was triturated with isohexanes and filtered to give 2,7-bis(1-ethoxyvinyl)phenazine as a brown solid (1.27 g, 88% yield). 1H NMR (CDCl3) δ 8.55-8.53 (2H, m), 8.19-8.15 (2H, m), 8.11-8.07 (2H, m), 4.98 (2H, d, J=3 Hz), 4.49 (2H, d, J=3 Hz), 4.03 (4H, q, J=7 Hz), 1.50 (6H, t, J=7 Hz) ppm. LC-MS (ESI): m/z 322.1 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through CELITE™545
  3. customthe volatiles were removed in vacuo
  4. customThe crude brown solid was triturated with isohexanes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-551d1ad62af34b7d93aa0d239dede8ef
Source dataset
uspto-grants-2015_10
Patent number
US09150554B2

Reaction notes

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