Methanol → HCID 86273098, compound

HRID 1497708Notes

Reaction equation

HRID 1497708 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]([CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[CH:5]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:27][C:28]1[C:32](B(O)O)=[C:31]([CH3:36])[O:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+].CO>O1CCOCC1.Cl[Pd]Cl.O>[CH3:27][C:28]1[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:5]3[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:31]([CH3:36])[O:30][N:29]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600048HCID 117600048, compound

Product 1

HCID 86273098HCID 86273098, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-Bromo-3-[(1-methyl-4-piperidyl)methyl]-4-phenyl-1,4-dihydroquinazolin-2-one (100 mg, 0.24 mmol), 3,5-dimethylisoxazole-4-boronic acid (51 mg, 0.36 mmol), Na2CO3 (77 mg, 0.73 mmol) in dioxane (1.6 ml) with MeOH (0.4 ml) and water (0.2 ml) 1,1′-Bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (17 mg, 0.02 mmol) is added. The mixture is stirred for 5 h at 80° C., concentrated in vacuo and the product purified by RP HPLC.

Workup

  1. additionis added
  2. concentrationconcentrated in vacuo
  3. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-dcbb8c9fb4d04cd1b3ec0f7c75a4e54f
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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