1-Chloroethyl chloroformate → 2-Methyl-5-(pyrrolidin-3-yloxy)-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

HRID 966508Notes

Reaction equation

HRID 966508 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:21]3[CH2:25][CH2:24][N:23](CC4C=CC=CC=4)[CH2:22]3)[CH:18]=2)[NH:13][C:12]=1[CH3:33])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:34]C(OC(Cl)C)=O.CCCCCC.C(OCC)(=O)C>ClCCCl>[ClH:34].[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:21]3[CH2:25][CH2:24][NH:23][CH2:22]3)[CH:18]=2)[NH:13][C:12]=1[CH3:33])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5213051-Chloroethyl chloroformateHCID 102036365-(1-benzyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterHCID 21226206Ethyl acetate hexane

Product 1

HCID 1317251792-Methyl-5-(pyrrolidin-3-yloxy)-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-(1-benzyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.118 g, 0.268 mmol, 1.0 eq.) was dissolved in dry 1,2-dichloroethane (5 mL) and treated with α-chloroethyl chloroformate (0.035 mL, 0.32 mmol, 1.2 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 1/1). After 2 hours, the reaction was concentrated in vacuo, redissolved in methanol (5 mL), and heated to reflux. After 4 hours, the crude hydrochloride salt was precipitated from methanol/ethyl acetate/hexane to afford a brown solid, which was carried directly to the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationthe reaction was concentrated in vacuo
  4. dissolutionredissolved in methanol (5 mL)
  5. temperatureheated to reflux
  6. waitAfter 4 hours
  7. customthe crude hydrochloride salt was precipitated from methanol/ethyl acetate/hexane
  8. customto afford a brown solid, which

Sources & evidence

ORD record
ord-b74598cbcb34481494e44e2944994566
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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