Sodium Iodide → 3-Iodo-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester

HRID 420971Notes

Reaction equation

HRID 420971 reaction equation
[Na+].[I-:2].ClN1C(=O)CCC1=O.[CH2:11]([O:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)=[CH:20][CH:19]=2)=[O:15])[CH3:12].[O-]S([O-])(=S)=O.[Na+].[Na+]>CC(C)=O>[CH2:11]([O:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([C:24]=1[I:2])=[CH:22][C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=1)=[CH:20][CH:19]=2)=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 57419913Ethyl 5-(4-(trifluoromethyl)phenyl)-1H-indole-2-carboxylate

Product 1

HCID 574199143-Iodo-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

NaI (2.04 g, 14 mmol) in acetone (10 mL) was added dropwise to a stirred solution of N-chlorosuccinimide (1.83 g, 14 mmol) in acetone (10 mL) protected from light. After 15 min, a solution of 5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester (3.80 g, 11 mmol; see step (a) above) in acetone (60 mL) was added dropwise, followed by stirring for 2 h at rt. The mixture was poured into Na2S2O3 (aq, 10%, 250 mL) and extracted with EtOAc (200 mL). The combined extracts were washed with NaHCO3 (aq, sat), water and brine, dried (Na2SO4) and concentrated. The residue was treated with petroleum ether to give the sub-title compound. Yield 4.88 g (93%).

Workup

  1. extractionextracted with EtOAc (200 mL)
  2. washThe combined extracts were washed with NaHCO3 (aq, sat), water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionThe residue was treated with petroleum ether

Sources & evidence

ORD record
ord-2726ce31a1a94c6d992276d562473f9f
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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