2-Pyrrolidone → 2-[3-(2-Oxopyrrolidin-1-yl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

HRID 1927287Notes

Reaction equation

HRID 1927287 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.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>COCCOC.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]>[O:28]=[C:24]1[CH2:25][CH2:26][CH2:27][N:23]1[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

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1359396462-(3-Bromobenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one

Product 1

HCID 1359396502-[3-(2-Oxopyrrolidin-1-yl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 61B (0.1 g, 0.282 mmol), pyrrolidin-2-one (0.048 g, 0.565 mmol) cesium carbonate (0.130 g, 0.395 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.026 g, 0.028 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.025 g, 0.043 mmol) in DME (2 mL) was heated in a microwave (Personal Chemistry SmithSynthesizer) at 200° C. for 60 minutes. The mixture was filtered evaporated. The residue was purified by chromatography on silica gel with 20% to 80% ethyl acetate in hexane to provide the desired product. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.01-2.08 (m, 2 H) 2.47 (t, J=8.09 Hz, 2 H) 3.81 (t, J=7.02 Hz, 2 H) 3.99 (s, 2 H) 5.67 (s, 1 H) 7.08 (d, J=7.63 Hz, 1 H) 7.30 (t, J=7.78 Hz, 1 H) 7.43-7.50 (m, 2 H) 7.66 (s, 1 H) 7.80-7.88 (m, 1 H) 8.04 (d, J=8.24 Hz, 1 H) 8.12 (d, J=7.93 Hz, 1 H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customThe residue was purified by chromatography on silica gel with 20% to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-35b014d22412404499d28f27a37f604b
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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