3-Nitrophenylboronic Acid → 6-(4-methoxyphenyl)-3-(3-nitrophenyl)-9H-pyrido[2,3-b]indole

HRID 341299Notes

Reaction equation

HRID 341299 reaction equation
Cl[C:2]1[CH:22]=[N:21][C:5]2[NH:6][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][CH3:20])=[CH:15][CH:14]=1)=[CH:9][CH:8]=3.[N+:23]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)([O-:25])=[O:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[NH:6][C:5]2[N:21]=[CH:22][C:2]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:31]=4)=[CH:3][C:4]3=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 461831983-chloro-6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indole

Product 1

HCID 461841576-(4-methoxyphenyl)-3-(3-nitrophenyl)-9H-pyrido[2,3-b]indoleYield 69%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

3-chloro-6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indole (50 mg, 0.16 mmol, 1 equiv.), 3-nitrophenylboronic acid (81 mg, 0.48 mmol, 3 equiv.), K3PO4 (136 mg, 0.64 mmol, 4 equiv.), S-PHOS (13.1 mg, 0.032 mmol, 0.2 equiv.), Pd(OAc)2 (4.0 mg, 0.016 mmol, 0.1 equiv.) are introduced in a schlenk tube which is flushed with N2. Freshly distilled dioxane (0.433 ml) is then injected and the reaction is carried out at 100° C. overnight. The mixture is filtered through celite and concentrated under reduced pressure. The crude product is purified over silica gel chromatography (eluant CH2Cl2/AcOEt 6:4). The white solid obtained is washed with methanol to give the product as a white solid (43 mg, 0.11 mmol) in 69% yield.

Workup

  1. customis flushed with N2
  2. filtrationThe mixture is filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified over silica gel chromatography (eluant CH2Cl2/AcOEt 6:4)
  5. customThe white solid obtained
  6. washis washed with methanol

Sources & evidence

ORD record
ord-c33189b364bf4cdaac7ef339b773dc62
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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