Potassium Carbonate → HCID 136387333, compound

HRID 718192Notes

Reaction equation

HRID 718192 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([N:16]3[C:20](=[O:21])[NH:19][C:18]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:17]3)=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>O.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>[CH3:15][C:14]1[N:13]=[C:12]([N:16]2[C:20](=[O:21])[NH:19][C:18]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:17]2)[CH:11]=[CH:10][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:31]2[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 136641686HCID 136641686, compound

Product 1

HCID 136387333HCID 136387333, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

1-(5-((2-Chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-neopentyl-1H-1,2,4-triazol-5(4H)-one (0.15 g, 0.40 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.11 g, 0.52 mmol), and K2CO3 (0.14 g, 1.04 mmol) were suspended in a solution of dioxane (2.0 mL) and water (0.40 mL). The suspension was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.05 g, 0.04 mmol) was added and the reaction mixture was stirred at 85° C. for 12 h, allowed to cool to RT, diluted with water (5 mL), and extracted with EtOAc (5×10 mL). The combined organics were dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 1-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-3-neopentyl-1H-1,2,4-triazol-5(4H)-one (0.124 g, 69%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.83 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.89 (d, J=8.8 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 6.65 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 2.38 (s, 2H), 2.33 (s, 3H), 0.98 (s, 9H); MS (ESI) m/z: 420.2 (M+H+).

Workup

  1. customThe suspension was sonicated
  2. customsparged with Ar for 10 min
  3. temperatureto cool to RT
  4. extractionextracted with EtOAc (5×10 mL)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-dff39e81ba4a4c8ba3e209927cb77d60
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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