Tetrahydrofuran → HCID 10177127, compound

HRID 1791473Notes

Reaction equation

HRID 1791473 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).

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-5e7bd16ba5f94b02b3b6a3c660acd8af
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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