Potassium Carbonate → HCID 58366265, compound

HRID 877412Notes

Reaction equation

HRID 877412 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[N:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=2)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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>[C:26]([C:24]1[N:25]=[C:20]([C:2]2[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=2)[CH:21]=[CH:22][CH:23]=1)#[N:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12379801Methyl 6-chloropyridazine-3-carboxylateHCID 177504686-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile

Product 1

HCID 58366265HCID 58366265, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 6-chloropyridazine-3-carboxylate (S49, 34 mg, 0.19 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (45 mg, 0.19 mmol), K2CO3 (51 mg, 0.39 mmol), and (Ph3P)4Pd (34 mg, 0.029 mmol) were slurried in DMF (0.3 M). The reaction vessel was evacuated and refilled with argon three times. The mixture was warmed at 85° C. for 16 h. The reaction mixture was cooled and diluted with EtOAc, washed with 9:1 NH4OH:saturated aqueous NH4Cl and saturated aqueous NaCl, and then dried over Na2SO4 Evaporation yielded the crude product that was purified by flash chromatography (SiO2, 1.5×14 cm, 20-100% EtOAc-hexanes) to afford the title compound (25 mg, 53%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 9.03 (d, 1H, J=8.1 Hz), 8.75 (d, 1H, J=8.7 Hz), 8.36 (d, 1H, J=8.7 Hz), 8.09 (t, 1H, J=7.9 Hz), 7.84 (d, 1H, J=7.6 Hz), 4.12 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 164.4, 158.2, 154.4, 151.7, 138.7, 133.9, 129.8, 128.7, 125.5, 125.4, 116.9, 53.6; HRMS-ESI-TOF m/z 241.0721 ([M+H]+, C12H8N4O2 requires 241.0720).

Workup

  1. customThe reaction vessel was evacuated
  2. additionrefilled with argon three times
  3. temperatureThe reaction mixture was cooled
  4. additiondiluted with EtOAc
  5. washwashed with 9:1 NH4OH
  6. dry with materialsaturated aqueous NH4Cl and saturated aqueous NaCl, and then dried over Na2SO4 Evaporation
  7. customyielded the crude product that
  8. customwas purified by flash chromatography (SiO2, 1.5×14 cm, 20-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-25e078e5232748e78fb1408e39753fae
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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