Dimethylformamide → HCID 11622890, compound

HRID 1821951Notes

Reaction equation

HRID 1821951 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CN(C)C=O.[C:12]([O:16][C:17]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=C2)=[O:18])([CH3:15])([CH3:14])[CH3:13].O1CCCC1>ClCCl>[C:12]([O:16][C:17]([C:19]1[CH:27]=[C:26]2[C:25](=[CH:21][CH:20]=1)[NH:24][CH:23]=[C:2]2[CH:1]=[O:5])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 11183550Tert-butyl 1H-indole-5-carboxylate

Product 1

HCID 11622890HCID 11622890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.4 ml (4.87 mmol) oxalylchloride are dissolved in a three-neck flask under nitrogen in 15 ml absolute dichloromethane and cooled to 0° C. Thereafter, 0.4 ml absolute dimethylformamide dissolved in 15 ml absolute dichloromethane is added. The mixture is stirred on ice cooling for 20 minutes, gas generation and the formation of a colorless precipitate being observed. Then, 1.00 g (4.64 mmol) tert-butylindole-5-carboxylate is added and the reaction mixture is allowed to heat to room temperature. Stirring is continued for another 20 min, the suspension is transferred using tetrahydrofurane to a round flask and concentrated on a rotary evaporator. The residue is taken up in 40 ml tetrahydrofurane, mixed with 50 ml 20% sodium acetate solution and heated under reflux for 30 minutes. After cooling down, 30 ml 5% sodium hydrogen carbonate solution are added, extracted three times using ethyl acetate, the volume of the combined organic phases is concentrated to about 150 ml and washed with saturated NaCl solution. The organic phase is dried on sodium sulfate and the solvent is removed on the rotary evaporator. Recrystallization of the crude product from n-hexane/ethyl acetate supplies the product as a solid.

Workup

  1. additionis added
  2. temperatureto heat to room temperature
  3. stirringStirring
  4. waitis continued for another 20 min
  5. concentrationconcentrated on a rotary evaporator
  6. additionmixed with 50 ml 20% sodium acetate solution
  7. temperatureheated
  8. temperatureunder reflux for 30 minutes
  9. temperatureAfter cooling down
  10. addition30 ml 5% sodium hydrogen carbonate solution are added
  11. extractionextracted three times
  12. concentrationthe volume of the combined organic phases is concentrated to about 150 ml
  13. washwashed with saturated NaCl solution
  14. customThe organic phase is dried on sodium sulfate
  15. customthe solvent is removed on the rotary evaporator
  16. customRecrystallization of the crude product from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-980a11a8c0f6494f910bf6a102ca0c66
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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