Heptane → HCID 66739076, compound

HRID 1028029Notes

Reaction equation

HRID 1028029 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=1[F:18].[Zn](CC)[CH2:20][CH3:21].CCCCCCC.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[CH2:20]([C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=1[F:18])[CH3:21]

Participants

7

Reactant 4

HCID 8900HeptaneHCID 516892Sodium BicarbonateHCID 51358280HCID 51358280, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 66739076HCID 66739076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 6-bromo-5-fluoro-1H-indole-1-carboxylate (1.57 g, 5.0 mmol) in dioxane (10 mL) was added a solution of Et2Zn in heptane (3.5 mL, 1.0M, 3.5 mmol) at room temperature. The mixture was kept stirring for 30 min at 90° C. and then cooled down to 0° C., into which saturated sodium bicarbonate was added dropwise. The mixture was then treated with water and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and evaporated. The resulting oil was passed through a silica plug and eluted with 10% ethyl acetate in hexane. The eluent was evaporated to give tert-butyl 6-ethyl-5-fluoro-1H-indole-1-carboxylate as an oil which was solidified upon standing (1.25 g, 95%).

Workup

  1. additionwas added dropwise
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. washeluted with 10% ethyl acetate in hexane
  6. customThe eluent was evaporated

Sources & evidence

ORD record
ord-daf3bcd4f6e2429996f4039065f8687a
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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