Triethylamine → HCID 59401345, compound

HRID 2060863Notes

Reaction equation

HRID 2060863 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[CH:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][C:19]2[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1)=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 59401345HCID 59401345, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-1-napthaldehyde (172 mg, 1.0 mmol) in DCM (10 mL) was added copper (II) diacetate (181 mg, 1.0 mmol), 4-cyanophenyl boronic acid (441 mg, 3.0 mmol), triethylamine (0.7 mL, 5.0 mmol) and 4 Å molecular sieves. After 48 h at rt the mixture was filtered. Solvent was removed in vacuo and the residue purified by column chromatography (EtOAc:isohexane 3:7). The resulting solid was washed with ether (10 mL) and filtered. The filtrate was concentrated in vacuo to give the title compound: δH (CDCl3) 7.06 (1H, d), 7.21 (2H, d), 7.49 (1H, t), 7.62-7.82 (3H, m), 7.96 (1H, d), 8.28 (1H, d), 9.36 (1H, d), 10.33 (1H, s).

Workup

  1. filtrationAfter 48 h at rt the mixture was filtered
  2. customSolvent was removed in vacuo
  3. customthe residue purified by column chromatography (EtOAc:isohexane 3:7)
  4. washThe resulting solid was washed with ether (10 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-514522277d0041b3af8b2e1248909f5b
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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