Phenylboronic Acid → HCID 46842005, compound

HRID 1846348Notes

Reaction equation

HRID 1846348 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([C:17]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:25](=[O:34])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:14]=[N:15][CH:16]=1>C([O-])([O-])=O.[Na+].[Na+].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>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([N:26]2[C:25](=[O:34])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]2[C:13]2[CH:14]=[N:15][CH:16]=[C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 46841857HCID 46841857, compound

Product 1

HCID 46842005HCID 46842005, compoundYield 37.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Phenylboronic acid (0.067 g, 0.55 mmol) and Pd(PPh3)4 (0.005 g) were added to a mixture of 2-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4(3H)-one (0.190 g, 0.46 mmol) in 2 M Na2CO3 (0.5 mL) and DME (15 mL). After refluxing for 5 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in CHCl3 and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 70% of EtOAc in heptane, afforded the title compound as a white solid (0.070 g, 37%). 1H-NMR (300 MHz, DMSO-d6): δ8.81 (s, 1H), 8.58 (s, 1H), 8.24 (d, J=8.1 Hz, 1H), 8.02 (s, 1H), 7.90-7.98 (m, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.61-7.70 (m, 1H), 7.43-7.58 (m, 9H). MS (APCI) m/z: 410 (M+H)+.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3
  4. washwashed with H2O
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 10% to 70% of EtOAc in heptane

Sources & evidence

ORD record
ord-ee82498460ab4b54881a52799279bb86
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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