1-Bromo-2-nitrobenzene → HCID 22405327, compound

HRID 1956338Notes

Reaction equation

HRID 1956338 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:27]=[CH:26][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][N:15]3[CH:23]=[CH:24][CH:25]=[C:14]3[CH2:13]2)=[O:11])=[CH:8][CH:7]=1)CCC.Br[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N+:43]([O-:45])=[O:44]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[N+:43]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[C:6]1[CH:7]=[CH:8][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][N:15]3[CH:23]=[CH:24][CH:25]=[C:14]3[CH2:13]2)=[O:11])=[CH:26][CH:27]=1)([O-:45])=[O:44]

Participants

5

Reactant 2

HCID 113411-Bromo-2-nitrobenzeneHCID 22861322HCID 22861322, compound

Product 1

HCID 22405327HCID 22405327, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3.0 g of 10,11-dihydro-10-[4-(tributylstannyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 200 mg of tetrakis(triphenylphosphine)palladium(O) and 2.0 g of 1-bromo-2-nitrobenzene in 200 ml of toluene is refluxed for 16 hours. The reaction mixture is filtered and the filtrate evaporated in vacuo to a residue which is purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane to give 1.2 g of the desired product as a solid. Mass spectrum: M+H:410.

Workup

  1. temperatureis refluxed for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated in vacuo to a residue which
  4. customis purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-7b8b1b9006a443ddaab719cc10f10543
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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