Methanol → 3-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)benzenamine

HRID 341300Notes

Reaction equation

HRID 341300 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]2[N:18]=[CH:19][C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)=[CH:21][C:12]3=2)=[CH:5][CH:4]=1.CO>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]2[N:18]=[CH:19][C:20]([C:22]4[CH:23]=[C:24]([NH2:28])[CH:25]=[CH:26][CH:27]=4)=[CH:21][C:12]3=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 461841576-(4-methoxyphenyl)-3-(3-nitrophenyl)-9H-pyrido[2,3-b]indole

Product 1

HCID 461841583-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)benzenamineYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-(4-methoxyphenyl)-3-(3-nitrophenyl)-9H-pyrido[2,3-b]indole (35 mg, 0.09 mmol, 1 equiv.), is dissolved in anhydrous THF (1 ml), MeOH (8 ml), and palladium on charcoal (10 mg, 0.009 mmol, 0.1 equiv.), are then added in an autoclave which is flushed with argon and then pressurized with H2 (10 bar). The reaction is carried out at room temperature for 16 hours. The mixture is then filtered over Mite and washed with AcOEt. The green solid obtained is washed with methanol to afford the product as a slightly green solid (26 mg, 0.07 mmol), in 79% yield.

Workup

  1. customis flushed with argon
  2. filtrationThe mixture is then filtered over Mite
  3. washwashed with AcOEt
  4. customThe green solid obtained
  5. washis washed with methanol

Sources & evidence

ORD record
ord-df18fe136c4e4c60a09cf37173a793e2
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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