1,1'-Carbonyldiimidazole → HCID 22611465, compound

HRID 843935Notes

Reaction equation

HRID 843935 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][C:26]1[CH:27]=[C:28]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]1[CH2:33][CH2:32][CH:31]([N:39]([CH3:41])[CH3:40])[CH2:30][C:29]2=1>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:25][C:26]3[CH:27]=[C:28]4[C:36](=[CH:37][CH:38]=3)[NH:35][C:34]3[CH2:33][CH2:32][CH:31]([N:39]([CH3:41])[CH3:40])[CH2:30][C:29]4=3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 742801H-Indole-5-Carboxylic AcidHCID 226115606-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 22611465HCID 22611465, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 43.5 mg (0.27 mMol) indole-5-carboxylic acid in 1.5 mL dimethylformamide were added 44.3 mg (0.27 mMol) carbonyldiimidazole resulting in immediate gas evolution. The reaction mixture was stirred for 4 hours at room temperature and then 60.0 mg (0.26 mMol) 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole were added. After 3 days the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 4:1 dichloromethane:2% ammonium hydroxide in methanol. Fractions shown to contain product were combined and concentrated under reduced pressure to give 66.7 mg (69%) of 6-(indol-5-oyl)amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole. The compound was converted to its corresponding hydrochloride salt, crystallizing from ethanol:diethyl ether.

Workup

  1. concentrationAfter 3 days the reaction mixture was concentrated under reduced pressure
  2. washeluting with 4:1 dichloromethane
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-871543cc23b648948be7c69fb441d46f
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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