Toluene → HCID 53713413, compound

HRID 1439920Notes

Reaction equation

HRID 1439920 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([CH2:14][CH2:15][CH:16]=O)[CH:10]=[C:9]([Cl:18])[CH:8]=2)=[O:4].[C:19]1([CH3:25])[CH:24]=CC=C[CH:20]=1>>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([CH2:14][CH2:15][CH:16]=[CH:5][C:3]([O:4][C:19]([CH3:20])([CH3:24])[CH3:25])=[O:2])[CH:10]=[C:9]([Cl:18])[CH:8]=2)=[O:4]

Participants

3

Reactant 2

HCID 1140TolueneHCID 10582514HCID 10582514, compound

Product 1

HCID 53713413HCID 53713413, compoundYield 82%

Procedure

A mixture of 6-chloro-4-(3-oxopropyl)indole-2-carboxylic acid methyl ester (12.0 g, 45.2 mmol) and (tert-butoxycarbonylmethylene)triphenylenephosphorane (18.7 g, 49.7 mmol)in toluene (500 mL) was refluxed for 1 h and concentrated. The residue was purified by silica gel column chromatography with 5:1 hexane/toluene to give 12.21 g of the title compound (82%): 1H NMR (CDCl3) δ9.03 (bs, 1H), 7.29 (d, 1H, J=1.7 Hz), 7.20 (d, 1H, J=2.0 Hz), 6.95 (d, 1H, J=2.0 Hz), 6.92 (dt, 1H, J=15.5, 6.6 Hz), 5.80 (dt, 1H, J=15.5, 1.7 Hz), 3.96 (s, 3H), 3.01 (dd, 2H, J=8.6, 7.3 Hz), 2.59 (dd, 2H, J=14.5, 6.6 Hz), 1.49 (s, 9H).

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography with 5:1 hexane/toluene

Sources & evidence

ORD record
ord-238908adc5a54f24b40952ae09f1edde
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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