Pyridine → HCID 11425515, compound

HRID 1063879Notes

Reaction equation

HRID 1063879 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:20][CH3:21])[C:18]=1[OH:19])[CH:14]=[O:15].N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:20][CH3:21])[C:18]=1[O:19][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 66827Phenylboronic Acid

Product 1

HCID 11425515HCID 11425515, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flask containing of dichloromethane (58 ml) was added powdered 4 A sieves (3.37 g, activated at 500° C. for 8 h), phenylboronic acid (3.53 g, 28.95 mmol), 3-chloro-4-hydroxy-5-methoxybenzaldehyde (1.08 g, 5.79 mmol), copper (II) acetate (1.05 g, 5.79 mmol), pyridine (2.33 ml, 28.95 mmol) and triethylamine (4.0 ml, 28.95 mmol). The reaction flask was fitted with a drying tube and stirred overnight at room temperature. Filtration through celite and removal of volatiles in vacuo followed by column chromatography (silica, 10% ethyl acetate in hexane) provided the title compound as a yellow solid (540 mg, 35%). 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.60 (s, 1H), 7.44 (s, 1H), 7.28 (t, j=8.0 Hz, 2H), 7.05 (t, j=7.2 Hz, 1H), 6.83 (d, j=8.4 Hz, 2H), 3.84 (s, 3H). M+1=263

Workup

  1. additionwas added
  2. customThe reaction flask was fitted with a drying tube
  3. filtrationFiltration
  4. customthrough celite and removal of volatiles in vacuo

Sources & evidence

ORD record
ord-bb26b94dac884e2bbcb42edd8858d5d8
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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