Toluene → HCID 59455053, compound

HRID 1401714Notes

Reaction equation

HRID 1401714 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]([CH2:14]C(C3C=CC=CC=3)=O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[C:25]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:27][CH2:28][CH3:29])=[O:26].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]([CH2:14]/[C:56](/[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:30]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 497799092-(2,8-Dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-phenylethanone

Product 1

HCID 59455053HCID 59455053, compound

Conditions

Temperature
100 °C

Procedure

2-(2,8-Dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-phenylethanone (100 mg, 3 mmol) was dissolved in 3 mL of toluene. (Carbethoxymethylene)triphenylphosphorane (200 mg, 0.56 mmol) was added and the reaction mixture was heated at 100° C. overnight. Solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (100-200) eluting with 2% MeOH-DCM. 1H NMR (CDCl3, oxalate salt) δ (ppm): 7.70 (m, 1H), 7.50 (m, 2H), 7.38 (m, 3H), 7.20 (m, 1H), 7.10 (m, 1H), 5.30 (m, 1H), 4.80 (s, 2H), 3.90 (m, 2H), 2.90 (m, 2H), 2.80 (m, 2H), 2.60 (s, 3H), 2.42 (s, 3H), 2.0 (m, 2H), 1.0 (t, 3H).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography (100-200)
  3. washeluting with 2% MeOH-DCM

Sources & evidence

ORD record
ord-ed1f7fb0e4764713a603f289be0ea2cd
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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