Potassium Carbonate → HCID 59854562, compound

HRID 2375944Notes

Reaction equation

HRID 2375944 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[CH:10]=[C:9](I)[NH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH:28]=[C:29]([C:9]2[NH:8][C:5]3=[N:6][CH:7]=[C:2]([Br:1])[C:3]([Cl:12])=[C:4]3[CH:10]=2)[CH2:30][CH2:31]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 598545525-Bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59854562HCID 59854562, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

To a mixture of 5-bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine (46 mg, 0.12 mmol), potassium carbonate (36 mg, 0.25 mmol), dichlorobis-(triphenylphosphine)palladium (9 mg, 0.01 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (42 mg, 0.13 mmol) were added degassed dioxane (4 mL) and water (1 mL), and the mixture was heated to reflux for 5 h. The reaction was evaporated under reduced pressure and the residue was dissolved in DCM and filtered. The DCM filtrate was evaporated and the crude product obtained was purified by chromatography on silica gel [Jones Flashmaster, 20 g/70 mL cartridge, eluting with DCM:methanol 100:0→99.5:0.5], yielding the title compound. MS (ES+): m/z 413.84 (100) [MH+]; HPLC: tR=6.95 min (ZQ2000, nonpolar—15 min).

Workup

  1. additionwere added
  2. customdegassed dioxane (4 mL) and water (1 mL)
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 5 h
  5. customThe reaction was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in DCM
  7. filtrationfiltered
  8. customThe DCM filtrate was evaporated
  9. customthe crude product obtained
  10. customwas purified by chromatography on silica gel [Jones Flashmaster, 20 g/70 mL cartridge, eluting with DCM:methanol 100:0→99.5:0.5]

Sources & evidence

ORD record
ord-e3164ee2d11f4fb2a0ddf60516f11115
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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