Methanol → HCID 22997489, compound

HRID 1166190Notes

Reaction equation

HRID 1166190 reaction equation
C([N:8]1[CH2:13][CH:12]=[CH:11][CH:10]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9]1)C1C=CC=CC=1.ClCCOC(Cl)=O.CO>ClC(Cl)C>[F:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:14][CH:10]1[CH:11]=[CH:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 123052-Chloroethyl chloroformateHCID 22997487HCID 22997487, compound

Product 1

HCID 22997489HCID 22997489, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-[(1-benzyl-1,2,3,6-tetrahydro-3-pyridinyl)methyl]-5-fluoro-1H-indole (500 mg, 1.57 mmol) in dichloroethane is treated with chloroethylchloro-formate (0.51 mL, 4.7 mmol), stirred at 80° C. for 4.5 hr, cooled and concentrated in vacuo to give a residue. The residue is treated with methanol, heated at reflux temperature overnight, cooled and concentrated in vacuo. The resultant residue is purified by column chromatography (10% MeOH/CH2Cl2+NH4OH) to give the title compound as a pale yellow solid, 240 mg (66%) mp 145° C. (dec.), identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. temperatureheated
  5. temperatureat reflux temperature overnight
  6. temperaturecooled
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by column chromatography (10% MeOH/CH2Cl2+NH4OH)

Sources & evidence

ORD record
ord-a8cd8c9e8cab4c278d71fd7d7cbc4f4b
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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