Pyridine → HCID 18456834, compound

HRID 1272189Notes

Reaction equation

HRID 1272189 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1C.[Br:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1.C(Cl)[Cl:29]>CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 2734318(3-Bromophenyl)boronic acidHCID 18440061HCID 18440061, compound

Product 1

HCID 18456834HCID 18456834, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

To a flask was charged with 3-hydroxy-4-methylphenylacetonitrile (32a; 0.92 g; 6.2 mmol), Cu(OAc)2 (1.3 g; 6.9 mmol), 3-bromobenzeneboronic acid (1.1 g; 5.5 mmol) and powdered 4 Å molecular sieves, was added CH2Cl2 (62 mL) followed by pyridine (2.5 mL; 31 mmol). The reaction was stirred at rt for 3 days. The suspension was filtered through a bed of CELITE®/silica gel and the solid washed with CH2Cl2. The combined filtrates were washed sequentially with 2N HCl (2×25 mL), NaHCO3 (25 mL), water and brine. The extracts were dried (MgSO4), filtered and evaporated. The crude product 76 was sufficiently pure to use in the next step.

Workup

  1. filtrationThe suspension was filtered through a bed of CELITE®/silica gel
  2. washthe solid washed with CH2Cl2
  3. washThe combined filtrates were washed sequentially with 2N HCl (2×25 mL), NaHCO3 (25 mL), water and brine
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c8cc4bcced894e5ab2b0c535cfc88cab
Source dataset
uspto-grants-2007_04
Patent number
US07208509B2

Reaction notes

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