Water → HCID 57531261, compound

HRID 1455137Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8](=[O:20])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH3:19])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[N:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:46]3[CH:47]=[CH:48][N:43]=[CH:44][CH:45]=3)[CH:3]=2)=[O:20])=[CH:12][C:13]=1[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-(3-bromo-phenyl)-2-(4-methoxy-3-methylphenyl)ethane-1,2-dione (0.25 g, 0.75 mmol) in dioxane is treated sequentially with tri-o-tolylphosphine (57 mg, 0.187 mmol), palladium (II) acetate (21 mg, 0.093 mmol), pyridine-4-boronic acid (139 mg, 1.125 mmol) and H2O, stirred at 100° C. for 4 h, cooled to room temperature and filtered. The filtrate is evaporated in vacuo. The resultant residue is purified by flash chromatography on silica gel (hexanes/EtOAc 3/7 as eluent), to afford the title compound as a yellow solid, 0.145 g (58% yield), identified by HNMR and mass spectral analyses. MS m/e (M+H)+ 332; 1H NMR (400 MHZ, CDCl3) δ 2.28 (s, 3H) 3.95 (s, 3H) 6.94 (d, 1H) 7.68 (m, 3H) 7.84 (m, 2H) 7.88 (m, 1H) 8.08 (m, 1H) 8.30 (m, 1H) 8.75 (m, 2H).

Workup

temperaturecooled to room temperature
filtrationfiltered
customThe filtrate is evaporated in vacuo
customThe resultant residue is purified by flash chromatography on silica gel (hexanes/EtOAc 3/7 as eluent)

Sources & evidence

ORD record: ord-10da1f186c584357add049f154db6cec
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482349B2

Reaction notes

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