Potassium Carbonate → Ethyl 4-{3-[4-amino-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate

HRID 1066180Notes

Reaction equation

HRID 1066180 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[OH:27].C(=O)([O-])[O-].[K+].[K+].[Cl:34][CH:35](Br)[CH2:36][CH3:37]>CC(C)=O>[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[O:27][CH2:37][CH2:36][CH2:35][Cl:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 21197991Ethyl 4-[3-(4-amino-3-hydroxybenzoyl)indol-1-yl]butanoate

Product 1

HCID 21197988Ethyl 4-{3-[4-amino-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-[3-(4-amino-3-hydroxybenzoyl)indol-1-yl]butanoate (30 g) was suspended in acetone (390 ml), potassium carbonate (23.8 g) and chlorobromopropane (24 ml) were added to the suspension. The mixture was stirred at room temperature for four hours. The reaction mixture was cooled and filtrated. The filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 22.8 g of ethyl 4-{3-[4-amino-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate as colorless prisms.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltrated
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-210b2caddaba4569a22cd31b5d22e886
Source dataset
uspto-grants-2001_06
Patent number
US06242449B1

Reaction notes

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