Dimethylformamide → HCID 86668148, compound

HRID 1026619Notes

Reaction equation

HRID 1026619 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CN(C)C=O.[CH3:12][O:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=C3)[CH:16]=1>ClCCl>[CH3:12][O:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=[C:2]3[CH:1]=[O:5])[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67107011HCID 67107011, compound

Product 1

HCID 86668148HCID 86668148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To anhydrous dichloromethane (35 mL) was added oxalyl chloride (0.23 mL, 2.71 mmol). N,N-dimethylformamide (0.27 mL, 3.48 mmol) was added at 0° C., and the mixture was stirred for 30 min at 0° C. To this reaction solution was added 2-(1H-indol-5-yl)isonicotinic acid methyl ester (0.44 g, 1.74 mmol) obtained in Preparation 36, which was then stirred for 1 h at room temperature. The solvent was removed, tetrahydrofuran (40 mL) and 20% aqueous ammonium acetate solution (30 mL) were added, and the mixture was heated for 30 min while being stirred under reflux. The reaction solution was cooled, ethyl acetate was added, and washed with aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was filtered, washed with ethyl acetate and dried to give 2-(3-formyl-1H-indol-5-yl)isonicotinic acid methyl ester.

Workup

  1. customobtained in Preparation 36, which
  2. stirringwas then stirred for 1 h at room temperature
  3. customThe solvent was removed
  4. additiontetrahydrofuran (40 mL) and 20% aqueous ammonium acetate solution (30 mL) were added
  5. temperaturethe mixture was heated for 30 min
  6. stirringwhile being stirred
  7. temperatureunder reflux
  8. temperatureThe reaction solution was cooled
  9. additionethyl acetate was added
  10. washwashed with aqueous sodium bicarbonate solution
  11. customThe organic layer was separated
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. filtrationThe resulting solid was filtered
  15. washwashed with ethyl acetate
  16. customdried

Sources & evidence

ORD record
ord-b929bd88c4714aeba8afac8d7309acae
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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