Oxalyl chloride → HCID 22603434, compound

HRID 2307929Notes

Reaction equation

HRID 2307929 reaction equation
C([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([C:26](O)=[O:27])=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)C.[C:29](Cl)(=[O:33])[C:30](Cl)=O>ClCCl.CN(C=O)C>[Cl:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[Cl:19])[CH2:12][N:7]1[C:8]2[C:4](=[CH:3][CH:11]=[CH:10][CH:9]=2)[C:5]([C:26](=[O:27])[NH:7][CH2:6][CH:5]2[O:33][CH2:29][CH2:30][CH2:4]2)=[C:6]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22603401HCID 22603401, compound

Product 1

HCID 22603434HCID 22603434, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of ethyl N-(3,4-dichlorobenzyl)-2-ethoxycarbonylindole-3-carboxylic acid (100 mg) in dichloromethane (4 ml) at ambient temperature, under argon, was added DMF (1 drop) and oxalyl chloride in dichloromethane (2M, 153 μl). The reaction was stirred at ambient temperature for 7 hours, then concentrated in vacuo and dissolved in dichloromethane (4 ml). Tetrahydrofurfurylamine (53 μl) was added, followed by triethylamine (71 μl) and the reaction stirred under argon for 16 hours. The reaction was diluted with dichloromethane (30 ml), washed with HCl (2M, 30 ml) and water (30 ml), dried (MgSO4) and concentrated in vacuo to give a crude residue which was purified by column chromatography, using ethyl acetate:iso-hexane as eluent (gradient 10/90-50/50), to give the product as an off-white solid (57 mg, 47%); M/z (+) 475.3 (MH+),

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in dichloromethane (4 ml)
  3. additionTetrahydrofurfurylamine (53 μl) was added
  4. stirringthe reaction stirred under argon for 16 hours
  5. additionThe reaction was diluted with dichloromethane (30 ml)
  6. washwashed with HCl (2M, 30 ml) and water (30 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a crude residue which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-905c9eba032f49189784b750fcb2cd23
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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