Sodium Iodide → HCID 67120034, compound

HRID 242183Notes

Reaction equation

HRID 242183 reaction equation
Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:15][CH2:16][CH3:17])[CH:3]=1.[CH3:18][C:19]1[C:23](B(O)O)=[C:22]([CH3:27])[O:21][N:20]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>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.O1CCOCC1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:2]([C:23]3[C:19]([CH3:18])=[N:20][O:21][C:22]=3[CH3:27])=[CH:3][C:4]([CH2:15][CH2:16][CH3:17])=[N:5]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 67120035HCID 67120035, compound

Product 1

HCID 67120034HCID 67120034, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

5-Bromo-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole (287 mg, 0.97 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (274 mg, 1.94 mmol), K2CO3 (806 mg, 5.83 mmol), sodium iodide (291 mg, 1.94 mmol) and Pd(PPh3)4 (90 mg, 0.08 mmol) were mixed with degassed dioxane (1 mL) and degassed H2O (1 mL) under nitrogen in a microwave vial. The reaction was heated at 150° C. for 20 min. The crude mixture was diluted with CH2Cl2 and washed with water. The organic phase was separated from the water phase, dried using a phase separator and evaporated. The crude product was purified on silica column (CH2Cl2:Et2O, 90:10) to give 4-(1-(4-methoxyphenyl)-3-propyl-1H-pyrazol-5-yl)-3,5-dimethylisoxazole (178 mg, 59%).

Workup

  1. customdegassed H2O (1 mL) under nitrogen in a microwave vial
  2. additionThe crude mixture was diluted with CH2Cl2
  3. washwashed with water
  4. customThe organic phase was separated from the water phase
  5. customdried
  6. customevaporated
  7. customThe crude product was purified on silica column (CH2Cl2:Et2O, 90:10)

Sources & evidence

ORD record
ord-edd66bc5a8c048a2a7bc4e98bebf3a9d
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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