Tetrahydrofuran → HCID 10177127, compound

HRID 2221244Notes

Reaction equation

HRID 2221244 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][C:8]1[CH:29]=[CH:28][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:10][CH:9]=1.C1C[O:33]CC1>>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[C:15]([C:1](=[O:5])[C:2]([OH:33])=[O:3])=[CH:14]2)=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 22032969HCID 22032969, compound

Product 1

HCID 10177127HCID 10177127, compoundYield 72%

Procedure

Oxalyl chloride (0.474 mL, 5.43 mmol) was added dropwise to a stirring solution of 1-(4-methylbenzyl)-5-phenyl-1H-indole (0.46 g, 1.55 mmol) in THF (15 mL) at room temperature over a period of 5 minutes under a nitrogen atmosphere. After the reaction mixture was stirred at room temperature for 4 hours, the reaction was quenched carefully with water. The aqueous mixture was extracted with ethyl acetate. The extract was washed with water, and brine, dried over anhydrous magnesium sulfate, and concentrated to give the title compound as a yellow solid (0.41 g, 72%), m.p: 195-196° C. Mass spectrum (ESI, [M+H]+) m/z 370. 1HNMR (400 MHz, DMSO-d6): δ 13.95 (br s, 1H), 8.68 (s, 1H), 8.41 (s, 1H), 7.63-7.66 (m, 3H), 7.56 (d, 1H, J=10.4 Hz), 7.47 (t, 2H, J=7.5 Hz), 7.35 (t, 1H, J=7.3 Hz), 7.22(d, 2H, J=8.1 Hz), 7.15(d, 2H, J=8.0 Hz), 5.56 (s, 2H), and 2.25 ppm (s, 3H). Elemental Analysis for C24H19NO3.0.3 H2O: Calculated: C, 76.91; H, 5.27; N, 3.74. Found: C, 76.85; H, 5.18; N, 3.61.

Workup

  1. customthe reaction was quenched carefully with water
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. washThe extract was washed with water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3105b52c24d748868d442ba78750e833
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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