Pyridine → HCID 10308203, compound

HRID 2099497Notes

Reaction equation

HRID 2099497 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:3]=[N:2]1.[C:12]1(B(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:20]1([N:1]2[CH:5]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)[CH:3]=[N:2]2)[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2545321-Naphthaleneboronic acidHCID 35789812-(1H-pyrazol-4-yl)pyridine

Product 1

HCID 10308203HCID 10308203, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2-(1H-pyrazol-4-yl)pyridine (292 mg, 2 mmol), 1-napthaleneboronic acid (690 mg, 4 mmol), Cu(OAc)2 (547 mg, 3 mmol) and pyridine (0.32 mL, 4 mmol) in dichloromethane (4 mL) was added 0.5 g of 4 Å molecular sieves. The resulting reaction mixture was stirred at ambient temperature under atmospheric conditions for 48 h, whereupon it was filtered through Celite, washing with dichloromethane. The reaction mixture was concentrated on to silica gel in vacuo and purified by liquid chromatography onto silica gel eluting with EtOAc:hex (2:8 to 3:7) to afford 2-[1-(1-naphthyl)-1H-pyrazol-4-yl]pyridine as a white solid. 1H NMR (CD3Cl, 300 MHz) δ 8.63-8.65 (1H, m), 8.39 (1H, s), 8.34 (1H, s), 7.94-7.99 (3H, m), 7.73 (1H, ddd), 7.53-7.64 (5H, m), 7.18 (1H, m). MS (ESI) 272 (M+H)+

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through Celite
  3. washwashing with dichloromethane
  4. concentrationThe reaction mixture was concentrated on to silica gel in vacuo
  5. custompurified by liquid chromatography onto silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-9e9b0df7f65a4304a72b4a5dee9b829a
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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