Ethyl Acetate → HCID 25127533, compound

HRID 1672763Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]3[N:18]=[C:19]([NH:22][CH2:23][CH3:24])[N:20]=[CH:21][C:10]=3[C:9]2=[O:25])[CH:7]=1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:23]([NH:22][C:19]1[N:20]=[CH:21][C:10]2[C:9](=[O:25])[N:8]([C:6]3[CH:7]=[C:2]([C:29]4[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=4)[CH:3]=[N:4][CH:5]=3)[CH2:17][C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]=2[N:18]=1)[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 21 (80.0 mg, 0.198 mmol) obtained in Example 21 was dissolved in 1,4-dioxane/water=4/1 (5 mL), and the mixture was stirred at 80° C. for 2 hours after adding 4-pyridineboronic acid (73.0 mg, 0.595 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 16.0 mg, 0.0198 mmol), and sodium carbonate (63.0 mg, 0.595 mmol). The reaction mixture was diluted by addition of ethyl acetate. Then, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by preparative TLC to give the title compound (Compound 22) (46.0 mg, 58%).

Workup

washThen, the organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe residue obtained upon concentration under reduced pressure
customwas then purified by preparative TLC

Sources & evidence

ORD record: ord-802414dcf0b1451cbeaf1e5aee7eb0ca
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

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