Potassium Carbonate → HCID 178439358, compound

HRID 2262691Notes

Reaction equation

HRID 2262691 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:9]([OH:16])=[N:8][C:5]2=[N:6][CH:7]=1.[CH3:18][C:19]1(C)[C:23](C)(C)OB(C(C)=C)O1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:1][C:2]1[C:3]([C:19]([CH3:23])=[CH2:18])=[C:4]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:9]([OH:16])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 178446218HCID 178446218, compound

Product 1

HCID 178439358HCID 178439358, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

6-Chloro-7-iodo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol (25 mg, 0.068 mmol) was added to a dried microwave tube, followed by 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (20 uL, 0.102 mmol), PdCl2(dppf) (5 mg, 0.0068 mmol), K2CO3 (33 mg, 0.238 mmol), dioxane (3 mL) and water (0.5 mL). The resulting mixture was heated in the microwave at 135° C. for 20 minutes. LCMS showed the starting material was consumed. To the reaction mixture was added saturated NaHCO3 (50 ml), and the product was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine (50 mL) and concentrated. The crude product was flushed through silica gel plug and then purified by reverse phase HPLC to give 19 mg of the title compound as a white powder. m/z=280.20 [M+H]+

Workup

  1. customwas consumed
  2. additionTo the reaction mixture was added saturated NaHCO3 (50 ml)
  3. extractionthe product was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer was washed with brine (50 mL)
  5. concentrationconcentrated
  6. customThe crude product was flushed through silica gel plug
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-8e5ec256c912432ca5fa87e73461b214
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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