Hydrogen Bromide → HCID 23119569, compound

HRID 1431981Notes

Reaction equation

HRID 1431981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([C:15]#[C:16][CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[BrH:30].C([O-])(O)=O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[Br:30][C:16]1[CH:15]=[C:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[N:18]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:17]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131727712HCID 131727712, compound

Product 1

HCID 23119569HCID 23119569, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 3-(p-methoxyphenylsulfonylamino)-1-propinyl 3,4,5-trimethoxy-phenyl ketone (2.02 g, 2.78 mmol, Example 94c) in CH2Cl2 (10 ml) a solution of HBr (732 μl, 1.5 equiv., 33% in acetic acid) is added at 4° C. The reaction mixture is stirred for 45 min at 4° C., and poured onto ice, saturated aqueous NaHCO3 solution and ethyl acetate. The organic layer is dried (MgSO4), the solvents are evaporated and the residue chromatographed on SiO2 with ethyl acetate/hexane (1:3) to yield the title compound (2.0 g, 86.3%) as a pink solid. 1H-NMR (300 MHz, DMSO-d6): 7.65 (d, J=1.9, 1H); 7.38 (d, J=9.0, 2H); 7.02 (d, J=9.0, 2H); 6.40 (m, 3H); 3.82 (s, MeO); 3.72 (s, MeO); 3.69 (s, 2MeO).

Workup

  1. dry with materialThe organic layer is dried (MgSO4)
  2. customthe solvents are evaporated
  3. customthe residue chromatographed on SiO2 with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-194e151c656c4f2fb392286cc75e9ac8
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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