2-(3-Bromobenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one → 3-[(5-Oxo-4,5-dihydropyrazolo[1,5-a]quinazolin-2-yl)methyl]benzonitrile

HRID 1927284Notes

Reaction equation

HRID 1927284 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][C:6]1[CH:19]=[C:9]2[NH:10][C:11](=[O:18])[C:12]3[C:17]([N:8]2[N:7]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[C:23]([Zn]C#N)#[N:24]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:18]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]2[N:7]=[C:6]([CH2:5][C:4]3[CH:3]=[C:2]([CH:22]=[CH:21][CH:20]=3)[C:23]#[N:24])[CH:19]=[C:9]2[NH:10]1

Participants

5

Reactant 2

HCID 1359396462-(3-Bromobenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-oneHCID 178514179HCID 178514179, compound

Product 1

HCID 1359396473-[(5-Oxo-4,5-dihydropyrazolo[1,5-a]quinazolin-2-yl)methyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 61B (0.075 g, 0.212 mmol), dicyanozinc (0.03 g, 0.254 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.021 mmol) in DMF (2 mL) was heated in a microwave (Personal Chemistry SmithSynthesizer) at 150° C. for 10 minutes. The mixture was evaporated and purified by chromatography on silica gel with 10% MeOH/CH2Cl2 to provide the desired product. 1H NMR (500 MHz, DMSO-d6) δ ppm 4.08 (s, 2 H) 5.76 (s, 1 H) 7.46 (t, J=7.63 Hz, 1 H) 7.53 (t, J=7.63 Hz, 1 H) 7.69 (dd, J=12.36, 7.78 Hz, 2 H) 7.79-7.88 (m, 2 H) 8.02 (d, J=7.93 Hz, 1 H) 8.12 (d, J=7.93 Hz, 1 H) 12.12 (s, 1 H).

Workup

  1. customThe mixture was evaporated
  2. custompurified by chromatography on silica gel with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2da2d1e35e0e42ac92ebbb9af9daf4ef
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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