Tetrahydrofuran → HCID 10245053, compound

HRID 2243168Notes

Reaction equation

HRID 2243168 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH:9]=[CH:8]2)[CH:2]=[CH2:3].[C:19](Cl)(=[O:23])[C:20](Cl)=[O:21].C1C[O:28]CC1>>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]1[CH2:18][CH2:17][CH2:16]1)[CH:9]=[C:8]2[C:19](=[O:23])[C:20]([OH:28])=[O:21])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 68550441HCID 68550441, compound

Product 1

HCID 10245053HCID 10245053, compound

Procedure

The crude 5-allyloxy-1-cyclobutylmethyl-1H-indole from Step 3 was dissolved in 0.5 mL anhydrous THF and 0.22 mL (2.5 mmol) oxalyl chloride was added. The reaction was mixed overnight on an orbital shaker. The reaction was concentrated and the crude product was redissolved in a minimum volume of dichloromethane. 0.8 mL 1N aqueous NaOH was added and the reaction was capped and shaken. The solution was acidified by the dropwise addition of 2N aqueous HCl and extracted with 1.6 mL dichloromethane. LC/MS (see Note 2) indicated that the reaction was not complete. The crude material was redissolved in 0.5 mL anhydrous THF, 0.16 mL

Workup

  1. additionThe reaction was mixed overnight on an orbital shaker
  2. concentrationThe reaction was concentrated
  3. dissolutionthe crude product was redissolved in a minimum volume of dichloromethane
  4. addition0.8 mL 1N aqueous NaOH was added
  5. customthe reaction was capped
  6. additionThe solution was acidified by the dropwise addition of 2N aqueous HCl
  7. extractionextracted with 1.6 mL dichloromethane
  8. dissolutionThe crude material was redissolved in 0.5 mL anhydrous THF

Sources & evidence

ORD record
ord-b71107f47a2145edac032df42782580a
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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