Water → HCID 56659892, compound

HRID 2042636Notes

Reaction equation

HRID 2042636 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20](=[O:23])[NH:21][N:22]=2)=[CH:13][CH:12]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cu]I>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20](=[O:23])[N:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[N:22]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 25070031Irdabisant

Product 1

HCID 56659892HCID 56659892, compoundYield 3.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

In a 50 mL round bottom flask, 6-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2H-pyridazin-3-one (250 mg, 0.71 mmol), 2-bromopyridine (105 μL, 1.07 mmol), copper(I)iodide (13.6 mg, 0.07 mmol), and potassium carbonate (296 mg, 2.14 mmol) in dimethylformamide (10 mL) was heated to reflux 14 h. The reaction was cooled and water (20 mL) was added. The sticky solids were filtered off and then partitioned between methylene chloride and water, separated, and dried over MgSO4. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 10 mg (2.4%) oil. MS m/z 391 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. filtrationThe sticky solids were filtered off
  4. custompartitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-222a1733d0d34f76bd733f4e24f6bd67
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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