Potassium Carbonate → HCID 178446213, compound

HRID 1668848Notes

Reaction equation

HRID 1668848 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.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[Cl:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[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 66827Phenylboronic AcidHCID 178446218HCID 178446218, compound

Product 1

HCID 178446213HCID 178446213, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

6-Chloro-7-iodo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol (190 mg, 0.52 mmol), phenylboronic acid (76 mg, 0.63 mmol), and (DPPF)PdCl2 (38 mg, 0.052 mmol) were added to a microwave vial equipped with stirbar. A septum was affixed to the vial and the vessel was purged with nitrogen for 5 min. Degassed dioxane (5 mL), and degassed 2 M K2CO3 (aq.) (1 mL, 2 mmol) were added by syringe, and the septum was replaced with a crimped vial cap. The reaction was heated to 135° C. for 20 min. The reaction mixture was diluted with EtOAc and water, and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative LCMS provided the title compound as a white solid (60 mg). The compound was characterized by LCMS (m/z=316.1 [M+H]+) and 1H NMR.

Workup

  1. customvial equipped with stirbar
  2. customwas purged with nitrogen for 5 min
  3. additionwere added by syringe
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-a1db7d0fa74547ed84dad18f45b3c651
Source dataset
uspto-grants-2011_08
Patent number
US07989469B2

Reaction notes

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