p-Toluenesulfonic acid → HCID 67055908, compound

HRID 2036804Notes

Reaction equation

HRID 2036804 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:11][OH:12])[CH2:9][OH:10])[CH:5]=[N:6][CH:7]=1.CO[C:15](OC)([CH3:17])[CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:8]2[CH2:11][O:12][C:15]([CH3:17])([CH3:16])[O:10][CH2:9]2)[CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 67055867HCID 67055867, compound

Product 1

HCID 67055908HCID 67055908, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-bromopyridin-3-yl)propane-1,3-diol (0.12 g, 0.51 mmol) in DCM was added 2,2-dimethoxypropane (0.107 g, 1.03 mmol) and a catalytic amount of p-TSA. The mixture was stirred at room temperature for 3 h. The reaction mixture was quenched by the addition of sat. NaHCO3 solution and the organic layer washed successively with water and brine. The organic layer was concentrated to provide the 3-bromo-5-(2,2-dimethyl-1,3-dioxan-5-yl)pyridine (0.1 g, 71.4%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.53 (m, 2H), 8.17 (t, 2H, J=2 Hz), 4.00-3.92 (m, 4H), 3.07-3.02 (m, 1H), 1.47 (s, 3H), 1.38 (s, 3H).

Workup

  1. customThe reaction mixture was quenched by the addition of sat. NaHCO3 solution
  2. washthe organic layer washed successively with water and brine
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a7199b4a009c4a689bd06a56cdbd8a22
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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