Ethyl Acetate → HCID 57891678, compound

HRID 1820888Notes

Reaction equation

HRID 1820888 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:30]=3[N:29]=[CH:28][CH:27]=[CH:26]4)(=[O:20])=[O:19])[CH:10]=2)O1.I[C:33]1[CH:38]=[CH:37][N:36]=[C:35]([S:39][CH3:40])[N:34]=1.C(OCC)(=O)C>C(=O)([O-])[O-].[K+].[K+].O.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>[CH3:40][S:39][C:35]1[N:36]=[C:37]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:30]=3[N:29]=[CH:28][CH:27]=[CH:26]4)(=[O:20])=[O:19])[CH:10]=2)[CH:38]=[CH:33][N:34]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 57891740HCID 57891740, compound

Product 1

HCID 57891678HCID 57891678, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave reaction tube, 8-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline (47, 70 mg, 0.16 mmol), 4-iodo-2-methylsulfanyl-pyrimidine (101 mg, 0.402 mmol), and tetrakis(triphenylphosphine)palladium(0) (9.3 mg, 0.008 mmol) were mixed in 1.0 M potassium carbonate in water (0.48 mL) and tetrahydrofuran (0.77 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 the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (50% ethyl acetate in hexane) to yield the desired product in light yellow solid (46, 10 mg, 0.023 mmol). MS(ESI) [M+H+]+=434.0.

Workup

  1. customthe two 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. concentrationConcentration under reduced pressure
  6. customafforded the crude material, which
  7. customwas purified by column chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-72fb4323141b4a6a8a6fb910b598b605
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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