Hydrochloric Acid → HCID 87516624, compound

HRID 1431980Notes

Reaction equation

HRID 1431980 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=2)[N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=1.C([Li])(C)(C)C.CN([CH:38]=[O:39])C.Cl>C(OCC)C.C1COCC1.C(OCC)(=O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([N:5]2[CH:6]=[C:2]([CH:38]=[O:39])[CH:3]=[C:4]2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 23119569HCID 23119569, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 87516624HCID 87516624, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4bromo-1-p-methoxyphenylsulfonyl-2-(3,4,5-trimethoxyphenyl)-pyrrole (0.30 g, 0.62 mmol, Example 94b) in ethyl ether/THF (5 ml, 1:1 v/v) tert-butyl-lithium (1.5 equiv., 1.7 M in pentane) is added at −78° C. The reaction mixture is stirred for 20 min at −78° C., and DMF (255 mg, 5 equiv.) is added drop wise. The reaction mixture is kept for 1 h at −78° C., allowed to come to 4° C., and poured onto ice, 1 M aqueous HCl and ethyl acetate. The organic layer is dried (MgSO4), the solvents are evaporated, and the residue chromatographed on SiO2 with ethyl acetate/hexane to yield the title compound (0.196 g, 73%) as a light yellow solid. 1H-NMR (300 MHz, DMSO-d6): 9.86 (s, CHO); 8.44 (d, J=1.9, 1H); 7.38 (d, J=9.0, 2H); 7.01 (d, J=9.0, 2H); 6.56 (d, J=1.9, 1H); 6.36 (s, 2H); 3.82 (s, MeO); 3.72 (s, MeO); 3.67 (s, 2MeO).

Workup

  1. waitThe reaction mixture is kept for 1 h at −78° C.
  2. customto come to 4° C.
  3. dry with materialThe organic layer is dried (MgSO4)
  4. customthe solvents are evaporated
  5. customthe residue chromatographed on SiO2 with ethyl acetate/hexane

Sources & evidence

ORD record
ord-23fe3cdfc32248d49f2a3c5715d6b510
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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