Pyridine → HCID 58914753, compound

HRID 1297804Notes

Reaction equation

HRID 1297804 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.N1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 7054IsatinHCID 2734370(3-Methoxyphenyl)boronic acid2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 58914753HCID 58914753, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Using a method similar to Preparation 38, with isatin (2.94 g, 20 mmol), 3-methoxyphenylboronic acid (6.08 g, 40 mmol), copper (II) acetate (3.63 g, 20 mmol), pyridine (3.2 ml, 40 mmol) and powdered 4A sieves (15-25 g) in dichloromethane (60 mL). Follow reaction by TLC (50% ethyl acetate/hexane). Stir mechanically for 1 day and add more powdered 4A sieves (10-15 g). Stir for 3 days and add 3-methoxyphenylboronic acid (1.52 g, 10 mmol), copper (II) acetate (1.82 g, 10 mmol), pyridine (1.6 ml, 20 mmol) and powdered 4A sieves (10-15 g). Workup and purify by flash chromotagraphy (dichloromethane) to provide 4.09 g (81%) of an orange solid. MS (ES): m/z=254 (M+1); 1H NMR (DMSO-d6): δ7.66-7.58 (m, 2H), 7.51 (t, 1H), 7.19 (t, 1H), 7.09-7.04 (m, 3H) 6.85 (d, 1H), 3.80 (s, 3H).

Workup

  1. customsimilar to Preparation 38
  2. additionadd more
  3. stirringStir for 3 days
  4. customWorkup and purify by flash chromotagraphy (dichloromethane)

Sources & evidence

ORD record
ord-2af61c472aa848e7a635b7c309261ecd
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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