Pyridine → HCID 11989077, compound

HRID 2375898Notes

Reaction equation

HRID 2375898 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 11989077HCID 11989077, compoundYield 209.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a one-neck round-bottom flask were added 5-bromo-1H-pyridin-2-one (696 mg, 4.00 mmol), phenylboronic acid (975 mg, 8.00 mmol), cupric acetate (1450 mg, 8.00 mmol), triethylamine (1120 μl, 8.00 mmol), pyridine (647 μl, 8.00 mmol), 4 Å molecular sieves (1056 mg) and methylene chloride (24 ml). The flask was loosely capped and the above mixture was stirred at rt in the atmosphere of air for 20 h. The mixture was filtered through a celite pad, washed with CH2Cl2. After concentration in vacuo, a green oil (2100 mg) was obtained, which was then purified by chromatography on silica gel (64 g) eluting with 1000 ml 20%, 2000 ml 40% and 1000 ml 50% EtOAc/hexane to obtain the title compound as a light-yellow wax-like material. 1H NMR (CDCl3, 400 MHz): δ=5.59 (d, 1H, J=9.6 Hz), 7.35-7.38 (m, 2H), 7.41-7.46 (m, 2H), 7.49-7.52 (m, 3H). MS(ES+): m/z 250.06/252.02 (100/97) [MH+]. HPLC: tR=2.71 min (ZQ2000, polar—5 min).

Workup

  1. customThe flask was loosely capped
  2. filtrationThe mixture was filtered through a celite pad
  3. washwashed with CH2Cl2
  4. concentrationAfter concentration in vacuo

Sources & evidence

ORD record
ord-3387c1355e4a45829791f0e78fc4e252
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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