Phenylboronic Acid → HCID 46841855, compound

HRID 1846346Notes

Reaction equation

HRID 1846346 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[N:16]=[CH:15][C:14]([C:17]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([CH:33]([CH2:35][CH3:36])[CH3:34])=[CH:29][CH:28]=3)[C:25](=[O:37])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:13][CH:12]=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>[CH:33]([C:30]1[CH:29]=[CH:28][C:27]([N:26]2[C:25](=[O:37])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]2[C:14]2[CH:15]=[N:16][CH:11]=[C:12]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:13]=2)=[CH:32][CH:31]=1)([CH2:35][CH3:36])[CH3:34]

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 46841556HCID 46841556, compound

Product 1

HCID 46841855HCID 46841855, compoundYield 46.3%

Reagents, catalysts & solvents 3

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

Procedure

Phenylboronic acid (0.058 g, 0.48 mmol) and Pd(PPh3)4 (0.004 g) were added to a mixture of 2-(6-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.175 g, 0.40 mmol) in 2 M Na2CO3 (0.4 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 0% to 60% of EtOAc in CH2Cl2, afforded the title compound as a white solid (0.080 g, 46%). 1H-NMR (300 MHz, DMSO-d6): δ8.75 (s, 1H), 8.68 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.91-7.99 (m, 1H), 7.79-7.90 (m, 2H), 7.61-7.69 (m, 1H), 7.32-7.50 (m, 7H), 7.17-7.25 (m, 2H), 2.52-2.63 (m, 1H), 1.33-1.54 (m, 2H), 1.10 (d, J=6.9 Hz, 3H), 0.53 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 432 (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 0% to 60% of EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-8363d46b07764d56a830b3a40b0efa80
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…