Water → HCID 23442326, compound

HRID 2119640Notes

Reaction equation

HRID 2119640 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]3[CH:12]=[N:13][N:14]([CH3:15])[C:6]3=[C:5](Cl)[C:4]=2[CH:3]=1.C([Sn]([CH2:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[C:34]#[N:35])(CCCC)CCCC)CCC.[OH2:39]>CN(C)P(N(C)C)(N(C)C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:15][N:14]1[C:6]2[C:5](=[O:39])[C:4]3[CH:3]=[C:2]([CH2:30][C:31]4[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=4)[C:34]#[N:35])[CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 962WaterHCID 14812181HCID 14812181, compoundHCID 23442366HCID 23442366, compound

Product 1

HCID 23442326HCID 23442326, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-bromo-9-chloro-1-methyl-1H-pyrazolo[4,3-b]quinoline (EXAMPLE 19, step 2, 800 mg, 2.70 mmol), 3-[(tributylstannyl)methyl]benzonitrile ((H. Azizian et al., J. Organomet. Chem., 1981, 215, 49), 1.21 g, 2.97 mmol), dichlorobis(triphenylphosphine)palladium (II) (189 mg, 0.27 mmol) in hexamethylphosphoramide (15 ml) was stirred at 70° C. for 14 h. After cooling to room temperature, water (150 ml) was added, and extracted with ethyl acetate (300 ml×3). The combined organic layer was washed with water (100 ml), dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1.5 to 1:1) to give 572 mg (64%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (300 ml×3)
  3. washThe combined organic layer was washed with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1.5 to 1:1)

Sources & evidence

ORD record
ord-1d51ff3aacec4b0d99acb4f00b578644
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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