Sodium Formate → HCID 86716499, compound

HRID 1501327Notes

Reaction equation

HRID 1501327 reaction equation
[C:1]1([C:7]2[N:11]3[N:12]=[C:13](Br)[CH:14]=[C:15]([O:16][CH3:17])[C:10]3=[N:9][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]3([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[Na+]>[Pd].CN(C=O)C.O.CO>[CH3:17][O:16][C:15]1[C:10]2[N:11]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:19]3[CH:20]=[CH:21][C:22]([C:25]4([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:28][CH2:27][CH2:26]4)=[CH:23][CH:24]=3)[N:9]=2)[N:12]=[CH:13][CH:14]=1

Participants

7

Reactant 2

HCID 2723810Sodium FormateHCID 86716498HCID 86716498, compound

Product 1

HCID 86716499HCID 86716499, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tert-butyl (1-{4-[3-phenyl-6-bromo-8-methoxyimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-7 (0.075 g, 0.14 mmol) and 5% palladium on carbon (0.007 g) in DMF (1 mL) was added a solution of sodium formate (0.074 g, 1.09 mmol, 8.0 eq) in water (0.2 mL). The resulting mixture was stirred at 80° C. for 3 h, diluted with MeOH (10 mL) and stirred at room temperature for 1 h. The resulting solution was filtered through a membrane filter, and the solids were washed with MeOH (1 mL). The resulting solution was diluted with EtOAc (25 mL), washed with water (2×25 mL), dried (Na2SO4 anh.) and concentrated under reduced pressure to give tert-butyl {1-[4-(8-methoxy-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate approximately 75% purity (0.058 g, 90%):

Workup

  1. customwas prepared in a manner analgous to
  2. stirringstirred at room temperature for 1 h
  3. filtrationThe resulting solution was filtered through a membrane
  4. filtrationfilter
  5. washthe solids were washed with MeOH (1 mL)
  6. additionThe resulting solution was diluted with EtOAc (25 mL)
  7. washwashed with water (2×25 mL)
  8. dry with materialdried (Na2SO4 anh.)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4be47b5e5abd47138897acdd31bd8f17
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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