1-Bromopropane → HCID 86723140, compound

HRID 868848Notes

Reaction equation

HRID 868848 reaction equation
[H-].[Na+].[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1.Br[CH2:14][CH2:15][CH3:16]>C1COCC1.O>[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:14][CH2:15][CH3:16])[N:5]=1

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 178506566HCID 178506566, compound

Product 1

HCID 86723140HCID 86723140, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH (60%, 197 mg, 4.92 mmol) was added to a solution of 3-iodoindazole (1.0 g, 4.1 mmol) in THF (20 mL) at 0° C., and the reaction stirred further for 30 min. Bromopropane (605 mg, 4.9 mmol) was added to the reaction at 0° C. The solution was heated to reflux and stirred overnight. It was then cooled, diluted with water, extracted with EtOAc (3×30 mL), and the organics were washed with brine, dried (Na2SO4), and concentrated. Purification by silica gel chromatography (10%-30% EtOAc/hexanes) gave 650 mg (56%) of the title compound as a yellow solid. The minor isomer was not isolated or characterized. 1H NMR (400 MHz, CDCl3): δ 0.93 (3H, t, J=7.2 Hz), 1.93-1.98 (2H, m), 4.35 (2H, t, J=7.2 Hz), 7.20 (1H, t, J=7.6 Hz), 7.36-7.49 (3H, m).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. stirringstirred overnight
  4. temperatureIt was then cooled
  5. extractionextracted with EtOAc (3×30 mL)
  6. washthe organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (10%-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-88248f6d4e7c4a07805ad1a4bc4c7527
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

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