4,5-Diphenyl-1-tritylimidazole → HCID 68815696, compound

HRID 2104960Notes

Reaction equation

HRID 2104960 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH2:42]([O:44][C:45]1[CH:46]=[C:47]([O:62][CH:63]([CH3:65])[CH3:64])[C:48]([F:61])=[C:49]([CH:60]=1)/[CH:50]=[N:51]/[C:52]1[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][CH:53]=1)[CH3:43]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([N:51]([CH2:50][C:49]3[CH:60]=[C:45]([O:44][CH2:42][CH3:43])[CH:46]=[C:47]([O:62][CH:63]([CH3:65])[CH3:64])[C:48]=3[F:61])[C:52]3[CH:59]=[CH:58][C:55]([C:56]#[N:57])=[CH:54][CH:53]=3)[N:10]([C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 41804394,5-Diphenyl-1-tritylimidazoleHCID 178418339ButyllithiumHCID 178466720HCID 178466720, compound

Product 1

HCID 68815696HCID 68815696, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 19.1 (100 mg, 0.216 mmol) in 3 mL THF at 0° C., was added BuLi (1.4 M in THF, 170 μL, 0.238 mmol). The mixture was stirred at 0° C. for 20 min, then a solution of Intermediate 7.3 (70.5 mg, 0.216 mmol) in 0.5 mL THF was added dropwise. The mixture was stirred at rt for 30 min, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 96 mg of Intermediate 19.2 as a white solid.

Workup

  1. stirringThe mixture was stirred at rt for 30 min
  2. customwas quenched with sat. NH4Cl
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-55cf5ad1fde8488695dab65471f7ce26
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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