3,5-Dimethylisoxazole-4-boronic acid → HCID 86273096, compound

HRID 1497704Notes

Reaction equation

HRID 1497704 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[CH:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:20][C:21]1[C:25](B(O)O)=[C:24]([CH3:29])[O:23][N:22]=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]>[CH3:20][C:21]1[C:25]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[CH:5]3[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:24]([CH3:29])[O:23][N:22]=1

Participants

5

Reactant 2

HCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600615HCID 117600615, compound

Product 1

HCID 86273096HCID 86273096, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 6-Bromo-3-methyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one (15 g, 50.44 mmol) in dioxane (200 mL) is added NaCO3 (5.03 g, 474 mmol) and 3,5-dimethylisoxazole-4-boronic acid (7.8 g, 55.498 mmol) and Pd(dppf)Cl2 (4.268 g, 5.044 mmol) then the mixture is refluxed at 100° C. overnight in dioxane (200 mL). The reaction is concentrated and was purified by chromatography on silica gel to give product.

Workup

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

Sources & evidence

ORD record
ord-9de4862c881b4b5092db805832e51815
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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