1,2-Dibromoethane → HCID 18399713, compound

HRID 2184817Notes

Reaction equation

HRID 2184817 reaction equation
BrCCBr.I[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH2:35]([N:42]1[C:50]2[CH:49]=[CH:48][N:47]=[C:46](Br)[C:45]=2[CH:44]=[CH:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O1CCCC1.CNC>O1CCCC1.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:35]([N:42]1[C:50]2[CH:49]=[CH:48][N:47]=[C:46]([CH:6]3[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]3)[C:45]=2[CH:44]=[CH:43]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

9

Reactant 5

HCID 78391,2-DibromoethaneHCID 521585Tris(furan-2-yl)phosphaneHCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylateHCID 18399758HCID 18399758, compoundHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 18399713HCID 18399713, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
65 °C

Procedure

0.16 ml of 1,2-dibromoethane is added at ambient temperature, under argon, to a suspension of 1.35 g of powdered zinc in 10 ml of tetrahydrofuran. The mixture is heated for 5 minutes at 65° C., then brought to ambient temperature, and 0.23 ml of trimethylsilyl is then added. After stirring the mixture for 30 minutes, a solution of 4.5 g of the compound obtained in Step 2 in 8 ml of tetrahydrofuran is slowly added, and then after 45 minutes a solution, prepared ex situ 10 minutes beforehand, of 0.2 g of Pd2(dba)3 and 0.2 g of P(2-furyl)3 in 5 ml of tetrahydrofuran is added by cannulation under argon and, finally, 5.5 g of 1-benzyl-4-bromo-1H-pyrrolo[3,2-c]pyridine in 30 ml of a 1/1 tetrahydrofuran/dimethylamine mixture are added. The reaction mixture is heated at 65° C. for 16 hours and then, after return to ambient temperature, filtered and concentrated in vacuo. Chromatography on silica gel (cyclohexane/ethyl acetate: 50/50) enables the expected product to be isolated.

Workup

  1. custombrought to ambient temperature
  2. addition0.23 ml of trimethylsilyl is then added
  3. waitafter 45 minutes a solution
  4. customprepared ex situ 10 minutes
  5. additionis added by cannulation under argon
  6. temperatureThe reaction mixture is heated at 65° C. for 16 hours
  7. filtrationafter return to ambient temperature, filtered
  8. concentrationconcentrated in vacuo
  9. customto be isolated

Sources & evidence

ORD record
ord-df3bbbc40a7c45daa3411f6697e2bb37
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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