3-Pyridinylboronic acid → 2-(3-Pyridin-3-ylbenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one

HRID 1927286Notes

Reaction equation

HRID 1927286 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.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1>COCCOC.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>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=2)[CH2:5][C:6]2[CH:19]=[C:9]3[NH:10][C:11](=[O:18])[C:12]4[C:17]([N:8]3[N:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:24]=1

Participants

5

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 1359396462-(3-Bromobenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one

Product 1

HCID 1359396492-(3-Pyridin-3-ylbenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 61B (0.05 g, 0.141 mmol), pyridine-3-ylboronic acid (0.018 g, 0.148 mmol) cesium fluoride (0.064 g, 0.423 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.1 g, 0.014 mmol) in DME (2 mL) was heated in a microwave (Personal Chemistry SmithSynthesizer) at 150° C. for 10 minutes. The mixture was filtered evaporated. The residue was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA to provide the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.10 (s, 2 H) 5.75 (s, 1 H) 7.41-7.51 (m, 3 H) 7.63-7.73 (m, 2 H) 7.76 (s, 1 H) 7.83-7.88 (m, 1 H) 8.04 (d, J=7.67 Hz, 1 H) 8.12 (dd, J=8.13, 1.38 Hz, 1 H) 8.35 (dt, J=7.98, 1.84 Hz, 1 H) 8.68 (dd, J=5.06, 1.38 Hz, 1 H) 9.01 (d, J=2.15 Hz, 1 H) 12.08 (s, 1 H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customThe residue was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA

Sources & evidence

ORD record
ord-65ca623987a84119ab9b175068811302
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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