Toluene → HCID 11994152, compound

HRID 1644837Notes

Reaction equation

HRID 1644837 reaction equation
C([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])[C:6]=1B(O)O)C(C)C.Br[C:23]1[CH:34]=[CH:33][C:26]([CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:25][CH:24]=1.[OH-].[Na+].[C:37]1([CH3:43])[CH:42]=CC=C[CH:38]=1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[N:28]1([CH2:27][C:26]2[CH:33]=[CH:34][C:23]([C:6]3[CH:5]=[C:10]([CH2:38][CH:37]([CH3:43])[CH3:42])[CH:9]=[CH:8][C:7]=3[S:11]([NH:14][C:15]([CH3:16])([CH3:17])[CH3:18])(=[O:12])=[O:13])=[CH:24][CH:25]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 29895571-(4-Bromobenzyl)-1H-imidazoleHCID 66775914HCID 66775914, compound

Product 1

HCID 11994152HCID 11994152, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude product from step (b) above (1.2 g, 3.83 mmol), 1-(4bromo-benzyl)-1H-imidazole (98.8 mg, 0.416 mmol, see Example 1(d) above), Pd(PPh3)4 (29 mg, 0.25 mmol), NaOH (3 mL, 1M, 3 mmol), toluene (15 mL) and ethanol (3 mL) were mixed under N2 (g). The mixture was heated to reflux for 2 h. The reaction mixture was then diluted with ethyl acetate (150 mL) and washed with water and brine. The organic phase was dried over MgSO4 and the solvent was removed in vacuo. Purification using column chromatography with CHCl3:MeOH (20:1) as eluent yielded the sub-title compound (93.7 mg, 0.220 mmol) in 53% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-4ea35a27056445319cc030e649bf30f7
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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