Oxalyl chloride → HCID 10070837, compound

HRID 1244799Notes

Reaction equation

HRID 1244799 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](Cl)(=[O:30])[C:27]([Cl:29])=[O:28]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH:13]=[C:12]2[C:26](=[O:30])[C:27]([Cl:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 10019598HCID 10019598, compound

Product 1

HCID 10070837HCID 10070837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-benzyloxy-1-(4-fluorobenzyl)indole in 200 ml of THF is cooled under a N2 atmosphere to 0° C. While stirring and cooling further, a solution of oxalyl chloride in 100 ml of THF is added dropwise in such a way that the internal temperature does not exceed 10° C. The reaction mixture is then boiled under reflux for 2 hours. The solvent is distilled out as completely as possible in vacuo at a bath temperature of 50–60° C. The crude product remains as residue and crystallizes on cooling. It is employed without further working up in the next reaction stage.

Workup

  1. temperaturecooling further
  2. customdoes not exceed 10° C
  3. temperatureunder reflux for 2 hours
  4. distillationThe solvent is distilled out as completely as possible in vacuo at a bath temperature of 50–60° C
  5. customcrystallizes
  6. temperatureon cooling
  7. customwithout further working up in the next reaction stage

Sources & evidence

ORD record
ord-e4bcd592df78452985b57dd6be5ae577
Source dataset
uspto-grants-2006_10
Patent number
US07122674B2

Reaction notes

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