3-chloro-6-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indole → 3-chloro-6-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)-9H-pyrido[2,3-b]indole

HRID 341296Notes

Reaction equation

HRID 341296 reaction equation
[Cl:1][C:2]1[CH:39]=[N:38][C:5]2[N:6](S(C3C=CC=CC=3)(=O)=O)[C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:15][CH:14]=1)=[CH:9][CH:8]=3>CO>[Cl:1][C:2]1[CH:39]=[N:38][C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)=[CH:17][CH:18]=1)=[CH:9][CH:8]=3

Participants

3

Reactant 1

HCID 461829703-chloro-6-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indole

Product 1

HCID 461834403-chloro-6-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)-9H-pyrido[2,3-b]indoleYield 83.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-chloro-6-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indole (203 mg, 0.36 mmol) is added to a solution of Na (83 mg, 3.6 mmol, 10 equiv.) in anhydrous MeOH (3.6 ml). The reaction is carried out at 65° C. for 2 hours, the mixture is then hydrolysed with ethanol and H2O and extracted with ethyl acetate (3×20 ml). The organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue (orange solid) is purified over flash chromatography (eluted with THF/MeOH 9:1) to give the product R347 as a white solid (124 mg, 0.30 mmol) in 83% yield. 1H NMR (300 MHz, (CD3)2C0) δ 12.01 (br s, 1H), 8.74 (d, 1H, J=2.3 Hz), 8.49 (d, 1H, J=1.7 Hz), 8.42 (d, 1H, J=2.5 Hz), 7.76 (dd, 1H, J=1.8, 8.5 Hz), 7.66 (d, 2H, J=8.9 Hz), 7.55 (d, 1H, J=8.5 Hz), 7.06 (d, 2H, J=8.9 Hz), 4.13 (t, 2H, J=5.8 Hz), 2.72 (t, 2H, J=5.8 Hz), 2.38 (br s, 8H).

Workup

  1. extractionhydrolysed with ethanol and H2O and extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue (orange solid) is purified over flash chromatography (eluted with THF/MeOH 9:1)

Sources & evidence

ORD record
ord-fb5510cd8d274104a67c03dafde53ef4
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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