Sodium Hydroxide → HCID 22718489, compound

HRID 1582656Notes

Reaction equation

HRID 1582656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br.BrC[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[C:13]([CH3:15])=[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]=2[CH:21]([CH3:22])[CH3:23])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 127522194-(Bromomethyl)pyridine hbrHCID 22718459HCID 22718459, compound

Product 1

HCID 22718489HCID 22718489, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A solution of 0.1 g of ethyl 5-(3,5-dichlorophenylsulphanyl)-4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate in 2 ml of anhydrous tetrahydroftiran was stirred at room temperature under nitrogen and treated with 65 mg of 4-bromomethylpyridine hydrobromide, 5 mg of tetra-n-butylammonium bromide and 24 mg of powdered sodium hydroxide. The mixture was stirred at room temperature for 20 h then diluted with 20 ml of water and extracted three times with 10 ml of ethyl acetate. Combined extracts were washed with 10 ml of brine, then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/isohexane (1:1) for the elution to give 0.104 g of ethyl 5-(3,5-dichlorophenylsulphanyl)-4-isopropyl-2-methyl-1-pyridin-4-yl-1H-pyrrole-3-carboxylate as a colourless gum. Mass spectrum (ESI) m/z 463 [M+H]+. 1H NMR (CDCl3) 1.32 (d, 6H), 1.40 (t, 3H), 2.45 (s, 3H), 3.61 (m 1H), 4.34 (q, 2H), 5.16 (s, 2H), 6.69 (d, 2H), 6.76 (m, 2H), 7.01 (t, 1H), 8.47 (m, 2H).

Workup

  1. extractionextracted three times with 10 ml of ethyl acetate
  2. washCombined extracts were washed with 10 ml of brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-73b4106f769e4dcb89386cb6a7990dbf
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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