Dichloromethane → ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate

HRID 420990Notes

Reaction equation

HRID 420990 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.C(Cl)Cl.[CH2:10]([O:12][C:13]([C:15]1[NH:16][C:17]2[C:22](C=1)=[CH:21][C:20]([Br:24])=[CH:19][CH:18]=2)=[O:14])[CH3:11].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:10]([O:12][C:13]([C:15]1[NH:16][C:17]2[C:18]([C:2]=1[CH:1]=[O:5])=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 3275613ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customCrystallisation from EtOH

Sources & evidence

ORD record
ord-fc01060092af47e990830d0e312becc8
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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