4-Nitrobenzyl bromide → HCID 57565267, compound

HRID 1727060Notes

Reaction equation

HRID 1727060 reaction equation
[C:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14].N12CCCN=C1CCCCC2>C(O)C.C1C=CC=CC=1.[Pd]>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:11][C:10]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:12])=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

7

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 842611H-Indene-3-carboxylic acid

Product 1

HCID 57565267HCID 57565267, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To a solution of 3H-Indene-1-carboxylic acid (2.0 g, 13.3 mmol) in ethanol (35 mL) was added 10% Pd/C (200 mg). The reaction mixture was stirred under an H2 atmosphere for 1 h. The mixture was filtered through Celite and concentrated in vacuo. The residue was combined with p-nitrobenzyl bromide (5.8 g, 26.8 mmoles) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.4 mL, 16.0 mmol) in 65 mL of benzene, and was stirred at 50° C. for 20 hours. After this period the heterogeneous mixture was gravity filtered and the filtrate was evaporated in vacuo. The residue was combined with CH2Cl2 and was washed with 1N HCl (2×25 mL) and sat'd NaHCO3 (2×25 mL), and the resulting CH2Cl2 solution was dried over anhydrous Na2SO4. The crude solid was purified using flash silica chromatography (0-10% EtOAc/Hexane) to yield 3.61 g (95%) of the intermediate.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. stirringwas stirred at 50° C. for 20 hours
  4. waitAfter this period the heterogeneous mixture was
  5. filtrationgravity filtered
  6. customthe filtrate was evaporated in vacuo
  7. washwas washed with 1N HCl (2×25 mL) and sat'd NaHCO3 (2×25 mL)
  8. dry with materialthe resulting CH2Cl2 solution was dried over anhydrous Na2SO4
  9. customThe crude solid was purified

Sources & evidence

ORD record
ord-4c30bf0f4ef745b884006c5b19a9e973
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

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