Toluene → HCID 58460235, compound

HRID 1946485Notes

Reaction equation

HRID 1946485 reaction equation
[CH3:1][CH:2]([C:4]1[NH:8][C:7]2[CH2:9][CH2:10][C:11](=[O:12])[C:6]=2[N:5]=1)[CH3:3].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:5]2[C:6]3[C:11](=[O:12])[CH2:10][CH2:9][C:7]=3[N:8]=[C:4]2[CH:2]([CH3:1])[CH3:3])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 58460155HCID 58460155, compound

Product 1

HCID 58460235HCID 58460235, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Tetrabutylammonium bromide (785 mg) was added to a stirred mixture of Intermediate 17 (800 mg), 4-chlorobenzyl bromide (1101 mg) in sodium hydroxide 20% aq. (9 mL) and toluene (20 mL). The RM was stirred at room temp under nitrogen atm. for 1.5 hours. Sat. NH4Cl aq solution (50 mL) was added and the mixture was extracted with EtOAc (2×50 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (467 mg). LC/MS MH+ 289, Rt 0.92 min (2 minute run).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 ml)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on silica using a cyclohexane
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6ae2879fdd642c78ed3e0d4255397be
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

Loading…