Dimethylformamide → 3-Isopropyl-6-(2-methyl-4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 2205726Notes

Reaction equation

HRID 2205726 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([CH3:13])[CH3:12])=[N:9][N:10]=2)[N:7]=1.[CH3:14][C:15]1[CH:20]=[C:19]([O:21][C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>C(OCC)(=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>[CH:11]([C:8]1[N:6]2[N:7]=[C:2]([C:16]3[CH:17]=[CH:18][C:19]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:20][C:15]=3[CH3:14])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 397324056-Chloro-3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 447176862-Methyl-4-(trifluoromethoxy)benzeneboronic acid

Product 1

HCID 509057543-Isopropyl-6-(2-methyl-4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave reaction tube was added 6-chloro-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine prepared as described in Step 1 above (1.28 mmole), 2-methyl-4-(trifluoromethoxy)phenylboronic acid (1.40 mmole), tetrakis(triphenylphosphine)palladium (0.064 mmole), 2M Na2CO3 (1 mL), and DMF (3 mL). The resulting reaction mixture was heated in the microwave at 130 C for 10 min. The reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude residue was purified by preparative HPLC to afford 3-isopropyl-6-(2-methyl-4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine.

Workup

  1. customTo a microwave reaction tube
  2. customprepared
  3. customThe resulting reaction mixture
  4. temperaturewas heated in the microwave at 130 C for 10 min
  5. filtrationfiltered through celite
  6. washThe filtrate was washed with water
  7. extractionThe organic extract
  8. dry with materialwas dried over Na2SO4
  9. customevaporated in vacuo
  10. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5dd589857e5448d2b6b986fbd0255dfa
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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