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

HRID 1846932Notes

Reaction equation

HRID 1846932 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-b409a2b9a50846f0ba13cb234dc65199
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

Loading…