Potassium Carbonate → (S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 388132Notes

Reaction equation

HRID 388132 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=CN=[C:12]([C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][CH:23]=[N:24]4)[CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C@@H](NC2[C:43]([N+:44]([O-])=O)=CN=C(Br)C=2)C)C=CC=CC=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.[C:61](=O)([O-])[O-:62].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C@@H:7]([N:9]2[C:10]3[C:15](=[N:44][CH:43]=[C:12]([C:19]4[CH:28]=[CH:27][CH:26]=[C:25]5[C:20]=4[CH:21]=[CH:22][CH:23]=[N:24]5)[CH:11]=3)[NH:16][C:61]2=[O:62])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 66699961((1S)-1-Phenylethyl)(5-nitro-2-(5-quinolyl)(4-pyridyl))amineHCID 86626410((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine

Product 1

HCID 67434577(S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-oneYield 77%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

((1S)-1-Phenylethyl)(5-nitro-2-(5-quinolyl)(4-pyridyl))amine. ((1S)-1-Phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine (5.6 g, 1.75 mmol) and 5-quinolineboronic acid (393 mg, 2.27 mmole) were dissolved in DMF (25 ml). Nitrogen gas was bubbled into solution for 2 min. Potassium carbonate (970 mg, 7.00 mmol) in water (5 mL) was then added followed by tetrakis(triphenylphosphine)palladium (0) (0.175 mmol). The solution was then heated to 85° C. under nitrogen for 1 h. The solution was condensed under reduced pressure and the crude product was diluted with ethyl acetate and filtered through a plug of silica-gel. The resultant filtrate was condensed under reduced pressure to afford the title compound (500 mg, 77%). MS (ESI) m/z 371 [M+1]+.

Workup

  1. customNitrogen gas was bubbled into solution for 2 min
  2. customcondensed under reduced pressure
  3. filtrationfiltered through a plug of silica-gel
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-66ee65722c13420ba064749378aa5f41
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

Loading…