Sodium Iodide → 2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 1-(acetyloxy)ethyl ester

HRID 1492491Notes

Reaction equation

HRID 1492491 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([OH:13])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([O:13][CH:49]([O:48][C:45](=[O:47])[CH3:46])[CH3:50])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 189503772-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid

Product 1

HCID 572504422-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 1-(acetyloxy)ethyl ester

Procedure

2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid (910 mg, 2.1 mmol, prepared as described in part C of Example 9), the title B compound (930 mg, 7.6 mmol), sodium iodide (795 mg, 5.03 mmol), cesium carbonate (2.6 g, 7.98 mmol) and dimethylformamide (4.0 mL) were combined and were stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate and filtered. The organic phase was washed with pH=4 buffer twice, pH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow oil. Purification by chromatography on Merck silica gel (250 g) eluting with (8:2) hexane/ethyl acetate gave the title B compound (1.06 g).

Workup

  1. filtrationfiltered
  2. washThe organic phase was washed with pH=4 buffer twice
  3. dry with materialpH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by chromatography on Merck silica gel (250 g)
  8. washeluting with (8:2) hexane/ethyl acetate

Sources & evidence

ORD record
ord-a345282878464c6a8a32c4d9636a29c7
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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