Oxygen → HCID 11548036, compound

HRID 1042572Notes

Reaction equation

HRID 1042572 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]2[C:7]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[O:16])=[C:8]([C:10]3[CH:11]=[N:12][NH:13][CH:14]=3)[O:9][C:5]=2[CH:4]=1.ClCCl.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.O=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]2[C:7]([C:15]([C:17]3[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=3)=[O:16])=[C:8]([C:10]3[CH:14]=[N:13][N:12]([C:39]4[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=4)[CH:11]=3)[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 6344DichloromethaneHCID 201262(4-Methoxyphenyl)boronic acidHCID 11661458HCID 11661458, compound

Product 1

HCID 11548036HCID 11548036, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an 8 mL screw cap glass vial was added [6-methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (11 mg, 0.027 mmol), 3 Å molecular sieves, dichloromethane (0.5 mL), cupric acetate (10 mg, 0.054 mmol), 4-methoxy-phenyl boronic acid (9 mg, 0.059 mmol) and pyridine (15 μL, excess) and the capped vial was shaken at room temperature for two days with occasional removal of the cap to expose the mixture to atmospheric oxygen. After this time the reaction mixture was filtered through celite and the filtrate was concentrated and purified by silica-gel flash chromatography (eluent=hexane:ethyl acetate, 3:1) to afford the product as a yellow solid (2 mg, 15% yield). 1H-NMR (CDCl3) δ 8.56 (s, 1H), 8.17 (s, 1H), 7.60 (d, J=8.9 Hz, 2H), 7.15 (s, 2H), 7.14 (d, J=8.7 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 6.96 (d, J=8.9 Hz, 2H), 6.81 (dd, J=8.7, 2.0 Hz, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 3.84 (s, 3H), 3.78 (s, 6H).

Workup

  1. customTo an 8 mL screw cap glass vial
  2. customcap
  3. filtrationAfter this time the reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica-gel flash chromatography (eluent=hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-60a829cb683146cfb4e3a55d3550d8bb
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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