1-Bromo-3,5-difluorobenzene → HCID 22405331, compound

HRID 1956339Notes

Reaction equation

HRID 1956339 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.[F:36][C:37]1[CH:38]=[C:39](Br)[CH:40]=[C:41]([F:43])[CH:42]=1>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]>[F:36][C:37]1[CH:38]=[C:39]([C:6]2[CH:7]=[CH:8][C:9]([C:10]([N:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[CH2:16][N:15]4[CH:23]=[CH:24][CH:25]=[C:14]4[CH2:13]3)=[O:11])=[CH:26][CH:27]=2)[CH:40]=[C:41]([F:43])[CH:42]=1

Participants

5

Reactant 2

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 22861322HCID 22861322, compound

Product 1

HCID 22405331HCID 22405331, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1.5 g of 10,11-dihydro-10-[4-(tributylstannyl)benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1 ml of 3,5-difluoro-1-bromobenzene and 200 mg of tetrakis(triphenylphosphine)palladium(O) 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 700 mg of the desired product as a solid. Mass spectrum: M+H:401.

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-c23490f04ee940aa88198142f427b920
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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