HCID 69221493, compound → HCID 10320267, compound

HRID 902032Notes

Reaction equation

HRID 902032 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:11]1[CH:20]=[C:19]2[C:14]([C:15]([C:21]3[C:22]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=4)=[N:23][N:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=34)=[CH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1>[Cl-].[Zn+2].[Cl-].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>[CH2:1]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([C:21]3[C:22]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=4)=[N:23][N:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=34)=[CH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 69221493HCID 69221493, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 10320267HCID 10320267, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Bubble nitrogen gas through 1 mL of THF for 10 minutes. Add benzyl magnesium chloride (2M in THF, 0.12 mL, 0.24 mmol), zinc chloride (1M in diethyl ether, 0.26 mL, 0.26 mmol). Bubble with nitrogen gas for 15 minutes. Add Pd(PPh3)2Cl2 (4 mg, 0.006 mmol), 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (0.05 g, 0.12 mmol). Stir at room temperature for 48 hours. Quench with aqueous saturated NH4Cl solution. Evaporate the solvent in vacuo. Add methylene chloride. Filter the mixture and concentrate the filtrate in vacuo. Chromatograph the residue on silica gel (elute with 50% ethyl acetate/hexanes then 100% ethyl acetate). Final purification by preparative HPLC affords the title compound 20 mg (40%) as a yellow foam.

Workup

  1. customBubble nitrogen gas through 1 mL of THF for 10 minutes
  2. customBubble with nitrogen gas for 15 minutes
  3. customQuench with aqueous saturated NH4Cl solution
  4. customEvaporate the solvent in vacuo
  5. filtrationFilter the mixture
  6. concentrationconcentrate the filtrate in vacuo
  7. washChromatograph the residue on silica gel (elute with 50% ethyl acetate/hexanes
  8. customFinal purification by preparative HPLC

Sources & evidence

ORD record
ord-b4327dbecb53467197ebc91912fe2d66
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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