Dimethylformamide → HCID 86611310, compound

HRID 1431970Notes

Reaction equation

HRID 1431970 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[N:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=1.C([Li])(C)(C)C.CN([CH:37]=[O:38])C>C(OCC)C>[C:13]1([CH3:16])[CH:14]=[CH:15][C:10]([S:7]([N:5]2[CH:6]=[C:2]([CH:37]=[O:38])[CH:3]=[C:4]2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68615328HCID 68615328, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86611310HCID 86611310, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromo-1-(p-toluenesulfonyl)-2-(3,4,5-trimethoxyphenyl)-pyrrole (2.33 g, 5.0 mmol) in dry ethyl ether (20 ml), a tert-butyl lithium solution (3.82 ml, 1.3 equiv., 1.7 M in pentane) is added at −78° C. The reaction mixture is stirred for 15 min at −78° C. DMF (1.93 ml, 5 equiv.) is added, and stirring continued at −78° C. for 2 h. The reaction mixture is slowly brought to 4° C., quenched with cooled aqueous 1 N HCl solution and ethyl acetate. The organic layer is extracted with brine, dried over MgSO4, the solvents evaporated and the residue chromatographed with gradients of hexane/ethyl acetate (2:1 to 1:1) to yield the title compound as a greenish solid. 1H-NMR (300 MHz, CDCl3): 9.9 (s, 1H); 8.13 (d, J=2.0 Hz, 1H); 7.3-7.1 (m, 4H); 6.57 (d, J=2.0 Hz, 1H); 3.36 (s, 2H); 6.36 (s, 2H); 3.92 (s, 3H); 3.76 (s, 6H); 2.39 (s, 3H).

Workup

  1. stirringstirring
  2. waitcontinued at −78° C. for 2 h
  3. customis slowly brought to 4° C.
  4. customquenched with cooled aqueous 1 N HCl solution and ethyl acetate
  5. extractionThe organic layer is extracted with brine
  6. dry with materialdried over MgSO4
  7. customthe solvents evaporated
  8. customthe residue chromatographed with gradients of hexane/ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-e9b5057f866e415d9de69c70ea7d6e45
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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