Ethanol → HCID 22032939, compound

HRID 1373346Notes

Reaction equation

HRID 1373346 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](Cl)(=[O:32])[C:29](Cl)=[O:30].[CH2:34]([OH:36])[CH3:35].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:28](=[O:32])[C:29]([O:36][CH2:34][CH3:35])=[O:30])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 22032903HCID 22032903, compound

Product 1

HCID 22032939HCID 22032939, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole (2.80 g, 7.62 mmol) in dry THF (40 mL) under nitrogen at 0° C. was added oxalyl chloride (2.0 mL, 23 mmol). The reaction mixture was stirred for one hour. It was cooled in an ice bath and ethanol (4.5 mL) was added. The reaction mixture was stirred for 25 minutes at room temperature then poured into excess aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated to dryness. The residue was purified by flash chromatography using 5–10% ethyl acetate in hexane as an eluant. Drying for 35 minutes at 60° C. yielded the title compound as a yellow gum (3.05 g, 86%): 1HNMR (300 MHz, DMSO-d6): δ8.75 (s, 1H), 8.45 (s, 1H), 7.8 (d, 2H, J=9.2 Hz), 7.75 (d, 1H, J=9.2 Hz), 7.6 (d, 1H, J=9.2 Hz), 7.45 (d, 2H, J=9.2 Hz), 7.3–7.4 (m, 5H), 5.85 (s, 2H), 4.35 (q, 2H, J=7.5 Hz), and 1.35 ppm (t, 3H, J=7.5 Hz).

Workup

  1. temperatureIt was cooled in an ice bath
  2. stirringThe reaction mixture was stirred for 25 minutes at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography
  8. customDrying for 35 minutes at 60° C.

Sources & evidence

ORD record
ord-5d325d4c906644af86cf74d6e9b9594a
Source dataset
uspto-grants-2007_01
Patent number
US07160918B2

Reaction notes

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