5-Methoxyindole-2-carboxylic acid → HCID 489420, compound

HRID 864433Notes

Reaction equation

HRID 864433 reaction equation
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([OH:26])=O)=[CH:18]2.C(N[C:31]1[C:32]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=N[CH:34]=[CH:35][CH:36]=1)CC.[C:43](=O)(O)[O-:44].[Na+]>O1CCCC1.CCOCC>[CH3:11][CH2:12][O:44][C:43]1[C:32]([N:37]2[CH2:38][CH2:39][N:40]([C:24]([C:19]3[NH:20][C:21]4[CH:22]=[CH:23][C:15]([O:14][CH3:13])=[CH:16][C:17]=4[CH:18]=3)=[O:26])[CH2:41][CH2:42]2)=[CH:31][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 204015-Methoxyindole-2-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 10331071HCID 10331071, compound

Product 1

HCID 489420HCID 489420, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1,1'-Carbonyldiimidazole (1.30 g) is added to a 20°-25° solution of 5-methoxyindole-2-carboxylic acid (I, 1.39) in tetrahydrofuran (14 ml). The reaction is stirred one hour, then cooled to 0° and 1-(2-ethoxyphenyl)piperazine (II, 1.50 g) dissolved in tetrahydrofuran (7 ml) is added via cannula. The reaction is warmed to 20°-25° and stirred 48 hours. The reaction is diluted with ether (100 ml), poured into saturated aqueous sodium bicarbonate (100 ml). The organic layers are separated and washed with saline (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from toluene to give the title compound, mp. 105°-107°.

Workup

  1. temperaturecooled to 0°
  2. additionis added via cannula
  3. temperatureThe reaction is warmed to 20°-25°
  4. stirringstirred 48 hours
  5. customThe organic layers are separated
  6. washwashed with saline (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-cc62814970994391a2a3a4fb4781e950
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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