Potassium Carbonate → HCID 86700371, compound

HRID 879548Notes

Reaction equation

HRID 879548 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7](B(O)O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[N:16]=1.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].CCOC(C)=O>[Br:14][C:15]1[N:16]=[C:17]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[N:3]=[CH:4]3)[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 225589101-Methyl-1H-indazole-5-boronic acid

Product 1

HCID 86700371HCID 86700371, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a 10-20 mL reaction vial, the 1-methyl-1H-indazol-5-ylboronic acid (500 mg, 2.73 mmol) and the 2,6-dibromopyridine (776 mg, 3.27 mmol) were dissolved in dioxane (7 mL) under argon atmosphere. The mixture was bubbled with argon for 5 min and then potassium carbonate (754 mg, 5.46 mmol) and PdCl2(dppf) catalyst were added sequentially. The resulting reaction mixture was then sealed and heated in oil bath at 110° C. for 3 h. Reaction was then diluted with EtOAc (10 mL), filtered and the filtrate was collected and concentrated. Residue was purified on silica gel column with 0-25% EtOAc/Hex to afford the title product. LCMS-ESI+: calc'd for: C13H10BrN3: 288.0, 290.0 (M+H+); Found: 288.2, 290.3 (M+H+).

Workup

  1. customIn a 10-20 mL reaction vial
  2. customThe mixture was bubbled with argon for 5 min
  3. customThe resulting reaction mixture
  4. customwas then sealed
  5. customReaction
  6. filtrationfiltered
  7. customthe filtrate was collected
  8. concentrationconcentrated
  9. customResidue was purified on silica gel column with 0-25% EtOAc/Hex

Sources & evidence

ORD record
ord-9bd0ba3cebec4360a58825856400a8d6
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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