(Z)-1-Ethoxy-2-(tributylstannyl)ethene → 1-[4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-3-chlorophenyl]-ethanone

HRID 2307395Notes

Reaction equation

HRID 2307395 reaction equation
C([Sn](CCCC)(CCCC)[CH:6]=[CH:7][O:8]CC)CCC.Br[C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH2:32][N:31]3[CH:39]=[CH:40][CH:41]=[C:30]3[CH2:29]2)=[O:27])=[C:22]([Cl:42])[CH:21]=1>C1(C)C=CC=CC=1>[CH:41]1[CH:40]=[CH:39][N:31]2[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N:28]([C:26]([C:23]3[CH:24]=[CH:25][C:20]([C:7](=[O:8])[CH3:6])=[CH:21][C:22]=3[Cl:42])=[O:27])[CH2:29][C:30]=12

Participants

4

Reactant 2

HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 9909050HCID 9909050, compound

Product 1

HCID 99509821-[4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-3-chlorophenyl]-ethanoneYield 26.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tributyl(ethoxyvinyl)tin (1.17 g) was added to a solution of (4-bromo-2-chlorophenyl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (1.24 g) in toluene (10 ml). The resultant solution was purged with nitrogen for 10 minutes, then bis(triphenylphosphine)palladium (II) chloride (0.11 g) was added. The reaction mixture was heated to reflux for 24 hours. The solution was cooled to room temperature and 5% aqueous hydrochloric acid (10 ml) was added. After stirring for one hour, the mixture was filtered through a pad of diatomaceous. Diethyl ether (5 ml) was added to the filtrate, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to yield a brown glass. Purification by flash chromatography on silica gel eluting with hexane-ethyl acetate (1:1) resulted in a white solid (0.30 g), MS, m/z: 364 (M)+.

Workup

  1. customThe resultant solution was purged with nitrogen for 10 minutes
  2. additionbis(triphenylphosphine)palladium (II) chloride (0.11 g) was added
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 24 hours
  5. addition5% aqueous hydrochloric acid (10 ml) was added
  6. filtrationthe mixture was filtered through a pad of diatomaceous
  7. additionDiethyl ether (5 ml) was added to the filtrate
  8. extractionthe resulting mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customto yield a brown glass
  13. customPurification by flash chromatography on silica gel eluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-26f6343d9c4f42ff86edfbc7a833affb
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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