Water → 8-[3-(2-Methoxy-pyrimidin-5-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline

HRID 1820887Notes

Reaction equation

HRID 1820887 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)(=[O:13])=[O:12])[CH:3]=1.[CH3:24][O:25][C:26]1[N:31]=[C:30](B(O)O)[CH:29]=[CH:28][N:27]=1.C(OCC)(=O)C.O>C(=O)([O-])[O-].[K+].[K+].O1CCCC1.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>[CH3:24][O:25][C:26]1[N:31]=[CH:30][C:29]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:11]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:23]=3[N:22]=[CH:21][CH:20]=[CH:19]4)(=[O:13])=[O:12])[CH:3]=2)=[CH:28][N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 45785507(2-Methoxypyrimidin-4-YL)boronic acidHCID 578916868-((3-Bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)sulfonyl)quinoline

Product 1

HCID 578917398-[3-(2-Methoxy-pyrimidin-5-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinolineYield 5.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave reaction tube, 8-(3-bromo-pyrrolo[2,3-b]pyridine-1-sulfonyl)-quinoline (44, 68 mg, 0.18 mmol), 2-methoxy-pyrimidine-4-boronic acid (67.4 mg, 0.438 mmol), and tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.0088 mmol) were mixed in 1.0 M of potassium carbonate (0.52 mL) and tetrahydrofuran (0.84 mL). The resulting mixture was heated at 120° C. in a CEM Discover microwave unit for 10 minutes. Ethyl acetate and water were added and two layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulfate. The product was concentrated under reduced pressure and the resultant crude material was purified by column chromatography (80-90% ethyl acetate in hexane) to yield the desired product as a white solid (43, 0.005 g, 0.01 mmol). MS(ESI) [M+H+]+=417.8.

Workup

  1. customtwo layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe product was concentrated under reduced pressure
  6. customthe resultant crude material was purified by column chromatography (80-90% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d70aadae4ed54938801efa7b624c8904
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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