Water → HCID 86700381, compound

HRID 879557Notes

Reaction equation

HRID 879557 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[C:15]1[N:16]([CH3:21])[CH:17]=[C:18]([Br:20])[N:19]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Br:20][C:18]1[N:19]=[C:15]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[N:3]=[CH:4]3)[N:16]([CH3:21])[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 72048802,4-Dibromo-1-methyl-1H-imidazoleHCID 225589101-Methyl-1H-indazole-5-boronic acid

Product 1

HCID 86700381HCID 86700381, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a 10-20 mL reaction vial, the 1-methyl-1H-indazol-5-ylboronic acid (169 mg, 0.966 mmol) and the 2,4-dibromo-1-methyl-1H-imidazole (300 mg, 1.25 mmol) were dissolved in dioxane (4 mL) and water (1 mL) under argon atmosphere. The mixture was bubbled with argon for 5 min and then potassium carbonate (400 mg, 2.895 mmol) and Pd(PPh3)4 (167 mg, 0.145 mmol) were added sequentially. The resulting reaction mixture was then sealed and heated in oil bath at 110° C. for 1.5 h. Reaction was then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase was washed with water (3×20 mL) and was concentrated. Residue was purified on silica gel column with 0-50% EtOAc/Hex to afford the desired product. LCMS-ESI+: calc'd for: C12H11BrN4: 291.0, 293.0 (M+H+); found: 291.0, 293.0 (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. customwas then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase
  7. washwas washed with water (3×20 mL)
  8. concentrationwas concentrated
  9. customResidue was purified on silica gel column with 0-50% EtOAc/Hex

Sources & evidence

ORD record
ord-220659e478524ecf93c4d01863e9485b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…