3,5-Dimethylisoxazole-4-boronic acid → HCID 86273097, compound

HRID 1497706Notes

Reaction equation

HRID 1497706 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[CH:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:21][C:22]1[C:26](B(O)O)=[C:25]([CH3:30])[O:24][N:23]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:21][C:22]1[C:26]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH3:14])[CH:5]3[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:25]([CH3:30])[O:24][N:23]=1

Participants

5

Reactant 2

HCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600799HCID 117600799, compound

Product 1

HCID 86273097HCID 86273097, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-Bromo-1,3-dimethyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one (100 mg, 0.3 mmol) in dioxane (3 mL) is added NaCO3 (50 mg, 0.45 mmol) and 3,5-dimethylisoxazole-4-boronic acid (56 mg, 0.39 mmol) and Pd(dppf)Cl2 then the mixture is refluxed at 100° C. overnight. The reaction is concentrated and is purified by chromatography on silica gel to give product.

Workup

  1. concentrationThe reaction is concentrated
  2. customis purified by chromatography on silica gel
  3. customto give product

Sources & evidence

ORD record
ord-c87f6ea9341c46f6b72110893b6bfd83
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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