Sodium hydride → HCID 87120903, compound

HRID 1470548Notes

Reaction equation

HRID 1470548 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Br:9][C:10]1[N:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=1>CS(C)=O>[CH2:21]([O:20][C:18]([C@@H:17]1[CH2:2][C@H:16]1[C:13]1[CH:14]=[N:15][C:10]([Br:9])=[CH:11][CH:12]=1)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11334330HCID 11334330, compound2×

Product 1

HCID 87120903HCID 87120903, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethyl sulfoxonium iodide (20.8 g, 94.7 mmol) was added in small portions to a suspension of sodium hydride (4 g, 170.6 mmol) in dry DMSO (400 mL) at rt., stirred for 1 h until clear solution was obtained. A solution of (E)-ethyl 3-(6-bromopyridin-3-yl)acrylate (Intermediate F, 20 g, 78.7 mmol) in dry DMSO (20 mL) was added and stirred for 4 h. After completion, the reaction mixture was poured into ice water (700 mL), extracted with EtOAc (2×350 mL). The combined organic extracts were washed with water (250 mL), brine (250 mL) and dried over anhydrous Na2SO4, filtered and evaporated to give (trans)-ethyl-2-(6-bromopyridin-3-yl)cyclopropanecarboxylate (10 g, 47° A)) as brown liquid.

Workup

  1. customwas obtained
  2. stirringstirred for 4 h
  3. extractionextracted with EtOAc (2×350 mL)
  4. washThe combined organic extracts were washed with water (250 mL), brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c0014c01423f49359b8821f443c35930
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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