Nitrogen → 4-[3-(2-furan-3-yl-pyridin-4-yl)-3H-imidazo[4,5-b]pyridin-5-ylamino]-cyclohexanol

HRID 1524193Notes

Reaction equation

HRID 1524193 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]3=[N:13][C:14]([NH:17][CH:18]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)=[CH:15][CH:16]=[C:11]3[N:10]=[CH:9]2)[CH:5]=[CH:4][N:3]=1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C([O-])([O-])=O.[Na+].[Na+].N#N>CCO.O>[O:25]1[CH:29]=[CH:28][C:27]([C:2]2[CH:7]=[C:6]([N:8]3[C:12]4=[N:13][C:14]([NH:17][CH:18]5[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]5)=[CH:15][CH:16]=[C:11]4[N:10]=[CH:9]3)[CH:5]=[CH:4][N:3]=2)=[CH:26]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 866518694-[3-(2-Chloro-pyridin-4-yl)-3H-imidazo[4,5-b]pyridine-5-ylamino]-cyclohexanol

Product 1

HCID 444760434-[3-(2-furan-3-yl-pyridin-4-yl)-3H-imidazo[4,5-b]pyridin-5-ylamino]-cyclohexanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 4-[3-(2-Chloro-pyridin-4-yl)-3H-imidazo[4,5-b]pyridine-5-ylamino]-cyclohexanol (1 eq, 100 mg, 0.29 mmol), 3-furyl boronic acid (1.05 eq, 0.3 mmol, 34 mg), Na2CO3 (2 eq, 0.58 mmol, 62 mg) in EtOH (2 ml) and H2O (0.7 ml) under inert atmosphere of N2 is added tetakis(triphenylphosphine) palladium (0.1 eq, 0.029 mmol, 21 mg). The reaction is heated in using microwave radiation at 80° C. for 2 hours. The mixture is diluted with H2O (5 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-2.5% MeOH in EtOAc to afford the title compound; [M+H]+ 375.

Workup

  1. temperatureThe reaction is heated
  2. customat 80° C.
  3. customfor 2 hours
  4. extractionextracted with EtOAc
  5. washThe combined organic portions are washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica eluting with 0-2.5% MeOH in EtOAc

Sources & evidence

ORD record
ord-847662492943457f8fb85cbc5723f9ba
Source dataset
uspto-grants-2015_07
Patent number
US09079897B2

Reaction notes

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