Potassium Carbonate → 5-(5-chloropyridazin-3-yl)-1-methyl-1H-indazole

HRID 879396Notes

Reaction equation

HRID 879396 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15](B(O)O)=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+]>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>[Cl:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[N:10]([CH3:9])[N:11]=[CH:12]3)[N:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 199596873,5-DichloropyridazineHCID 225589101-Methyl-1H-indazole-5-boronic acid

Product 1

HCID 867002035-(5-chloropyridazin-3-yl)-1-methyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

3,5-dichloropyridazine (200 mg, 1.34 mmol), 1-methyl-1H-indazole-5-boronic acid (260 mg, 1.48 mmol), K2CO3 (556.6 mg, 4.03 mmol), and tetrakis(triphenylphosphine)palladium(0) (233, 0.20 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (10 mL) and degassed water (2.5 mL). The reaction mixture was heated at 95° C. for 2 h then cooled to room temperature. The reaction mixture was filtered through Celite (ethyl acetate eluent) and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+: calc'd for C14H10ClN4: 245.1 (M+H+); Found: 245.2 (M+H+). 1H NMR (400 MHz, Chloroform-d) δ 9.15 (d, J=2.2 Hz, 1H), 8.44 (s, 1H), 8.21 (dd, J=8.8, 1.5 Hz, 1H), 8.11 (s, 1H), 7.97 (s, 1H), 7.56 (d, J=8.8 Hz, 1H), 4.14 (s, 3H).

Workup

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed 1,4-dioxane (10 mL)
  4. customdegassed water (2.5 mL)
  5. temperaturethen cooled to room temperature
  6. filtrationThe reaction mixture was filtered through Celite (ethyl acetate eluent)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  9. customprovided the product

Sources & evidence

ORD record
ord-93210446a980437181a609f7022fb7f9
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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