Water → HCID 59497321, compound

HRID 1747432Notes

Reaction equation

HRID 1747432 reaction equation
C([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20])=[O:5])C.[C:21](=O)([O-])[O-].[K+].[K+].[I-].[NH4+].N1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=C1.O.[CH3:39][N:40]([CH:42]=O)[CH3:41]>>[CH3:39][N:40]1[C:41]2[C:37](=[C:36]([CH3:21])[CH:35]=[CH:34][CH:33]=2)[C:32]([CH2:31][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]([C:7]3[CH2:8][CH2:9][CH2:10][C:6]=3[C:4]([OH:3])=[O:5])[C:12]2=[O:20])=[CH:42]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59497633HCID 59497633, compoundHCID 67361249HCID 67361249, compound

Product 1

HCID 59497321HCID 59497321, compoundYield 76%

Conditions

Temperature
100 °C

Procedure

To a solution of 100 mg (0.37 mmol) of 2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclopent-1-enecarboxylic acid ethyl ester in 5 mL of DMF was added 101 mg (0.73 mmol, 2.0 eq.) of potassium carbonate followed by 190 mg (0.55 mmol, 1.5 eq.) indole ammonium iodide at room temperature under nitrogen atmosphere. The resulting suspension was heated to 100° C. for 4 hours. The solution was cooled and stirred at RT over night. The reaction was poured into water and extracted with EtOAc (3×). The combined organics were washed with water, brine and dried (magnesium sulfate). Filtration and concentration gave the crude product which was absorbed onto silica gel and purified via CombiFlash to give 120 mg (76%) of the desired product as a light yellow oil.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationFiltration and concentration
  6. customgave the crude product which
  7. customwas absorbed onto silica gel
  8. custompurified via CombiFlash

Sources & evidence

ORD record
ord-3d9aa6eee4a5407fbfc2b83740cbd2a1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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