Potassium Hydroxide → HCID 178461480, compound

HRID 2092091Notes

Reaction equation

HRID 2092091 reaction equation
Br[C:2]1[C:3](=[O:25])[N:4]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].[OH-:26].[K+].[Cl-].[NH4+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>[OH:26][C:2]1[C:3](=[O:25])[N:4]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 68431637HCID 68431637, compound

Product 1

HCID 178461480HCID 178461480, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

4-Bromo-2-(tetrahydro-2H-pyran-2-yl)-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (200 mg, 0.49 mmol), tris(dibenzylideneacetone)dipalladium (9 mg, 0.01 mmol), potassium hydroxide (82 mg, 1.46 mmol) and 2-di-t-butylphosphino-2′,4′,6′-triisopropylbiphenyl (17 mg, 0.04 mmol) in 1,4-dioxane-water (1/1) were stirred in an argon stream at 100° C. for 1 hour. After completion of the reaction, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with chloroform three times, and the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to give the desired product (170 mg, 100% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform three times
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-9e9a9c6e4d5845dcaeea6bfaaf899098
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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