Bromine → HCID 59200639, compound

HRID 1258429Notes

Reaction equation

HRID 1258429 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C([Li])(C)(C)C.[Br:26]Br>C1COCC1.CCCCC>[Br:26][C:8]1[C:7]([O:9][CH3:10])=[CH:6][N:5]=[C:4]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 24408BromineHCID 59200629HCID 59200629, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59200639HCID 59200639, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dimethoxy-2-(4-methoxyphenylethynyl)pyridine M (120 mg, 0.446 mmol) in dry THF (2.5 ml) at −78° C. was added t-butyllithium (0.49 mmol, 0.30 ml of a 1.6M solution in pentane) and the reaction stirred for 10 minutes. After this time bromine (25 μL, 0.50 mmol) was added neat and the reaction was allowed to warm to room temperature and quenched by the addition of water (10 ml) and ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), dried over MgSO4 and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 3:1) to afford the product as a white solid (45 mg, 29%). 1HNMR (300 MHz, CDCl3) δ 7.99 (s, 1H), 7.52 (d, J=8.7 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 4.05 (s, 3H), 4.01 (s, 3H), 3.82 (s, 3H).

Workup

  1. customquenched by the addition of water (10 ml) and ethyl acetate (10 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 3:1)

Sources & evidence

ORD record
ord-7e11769511324a96b40c657e6c817337
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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