1,3-Dibromobenzene → HCID 71138602, compound

HRID 1852918Notes

Reaction equation

HRID 1852918 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.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]>[Br:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 79271,3-DibromobenzeneHCID 14451564-AcetamidopiperidineHCID 23676156Sodium t-butoxide

Product 1

HCID 71138602HCID 71138602, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,3-dibromobenzene (7.98 mL, 49.2 mmol), N-(4-piperidyl)acetamide (7.00 g, 49.2 mmol), Pd2(dba)3 (2.25 g, 2.46 mmol), (rac)-BINAP (2.30 g, 3.69 mmol) and sodium tert-butoxide (5.68 g, 59.1 mmol) in toluene (492 mL) was heated at 80° C. for 17 hours under nitrogen. After cooling to room temperature, the mixture was diluted with EtOAc and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (hexane/AcOEt=50:50 to 0:100) to afford the desired product (11.6 g, 80%) as pale orange solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through a Celite pad
  3. concentrationThe combined filtrate and washings were concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane/AcOEt=50:50 to 0:100)

Sources & evidence

ORD record
ord-cbcbb6cbff4041d6861d8a02301dfe8f
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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