Water → 4-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[[2'-(N-triphenylmethyl-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-1H-imidazole-5-carboxaldehyde

HRID 248641Notes

Reaction equation

HRID 248641 reaction equation
[C:1]1([C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:39][C:40]1[N:41]([C:46]2[N:47]=[C:48]([CH2:53][CH2:54][CH3:55])[NH:49][C:50]=2[CH:51]=[O:52])[C:42]([CH3:45])=[CH:43][CH:44]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:39][C:40]1[N:41]([C:46]2[N:47]=[C:48]([CH2:53][CH2:54][CH3:55])[N:49]([CH2:25][C:22]3[CH:21]=[CH:20][C:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[C:12]4[N:8]([C:7]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:9]=[N:10][N:11]=4)=[CH:24][CH:23]=3)[C:50]=2[CH:51]=[O:52])[C:42]([CH3:45])=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 149628924-(2,5-dimethyl-1H-pyrrol 1-yl)-2-propylimidazole-5-carboxaldehyde

Product 1

HCID 191069204-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[[2'-(N-triphenylmethyl-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-1H-imidazole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(triphenylmethyl)-5-[4'-(bromomethyl)-biphenyl-2-yl]tetrazole (Example 12, 9.66 g, 17.34 mmol), 4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propyl-1H-imidazole-5-carboxaldehyde (Example 49, 4.0 g, 17.4 mmol), and cesium carbonate (13 g, 40 mmol) in DMF (30 mL) was stirred under an atmosphere of dry nitrogen at room temperature overnight. The reaction mixture was poured over water (750 mL) and the resulting precipitate was collected by filtration. The solid was taken up in ethyl acetate and extracted with water, adjusting the pH of the aqueous layer to pH 8-9 by the addition of sodium bicarbonate. The organic layer was dried over MgSO4 and evaporated to give the crude product as a mixture of regioisomers which were separated by flash chromatography (silica; 3:1 hexane/EtOAc).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. extractionextracted with water
  3. additionby the addition of sodium bicarbonate
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-16faa76c740040ebb5a93e153052a4a2
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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