2-Bromopentane → HCID 86686447, compound

HRID 2176810Notes

Reaction equation

HRID 2176810 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:21]([CH2:23][CH2:24][CH3:25])[CH3:22]>>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:21]([CH2:23][CH2:24][CH3:25])[CH3:22])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 78902-BromopentaneHCID 146245-BenzyloxyindoleHCID 24758Sodium hydride

Product 1

HCID 86686447HCID 86686447, compoundYield 30%

Conditions

Temperature
-78 °C

Procedure

95% NaH (2.15 g, 89.0 mmol) and 5-benzyloxyindole (7) (10.0 g, 44.8 mmol) were added to a schlenk vessel, and the system was evacuated and refilled with nitrogen three times before being cooled to −78° C. DMF (100 mL) was added and the vessel was then cooled with an ice/water bath and kept stirring for another 30 min. 2-Bromopentane (2) (10.2 g, 67.2 mmol) was added dropwise and the resulting mixture was warmed to room temperature slowly and kept stirring overnight. The solvent was removed in vacuo. Toluene (200 mL) was added and the mixture was washed with water (150 mL) and dried with Na2SO4. After solvent was removed in vacuo, the resulting oil was purified using silica column chromatography (1:1 chloroform/hexanes) to give 5-(benzyloxy)-1-(pentan-2-yl)-1H-indole (8) (3.90 g, 30%) as an oil. 1H NMR (500 MHz, CDCl3): δ 7.51 (d, J=7.5, 2H), 7.41 (t, J=8.0 Hz, 2H), 7.35-7.20 (m, 2H), 7.18 (dd, J=8.0, 2.0, 2H), 6.97 (dd, J=9.0, 2.5, 1H), 6.41 (d, J=3.0, 1H), 5.13 (s, 2H), 4.46 (m, 1H), 1.87 (m, 2H), 1.55 (d, J=7.5, 3H), 1.26 (m, 2H), 0.90 (t, J=7.5, 3H). See also Luo, J.; Hart, H.; J. Org. Chem., 52(22): 4833 (1987).

Workup

  1. customthe system was evacuated
  2. additionrefilled with nitrogen three times
  3. additionDMF (100 mL) was added
  4. temperaturethe vessel was then cooled with an ice/water bath
  5. temperaturethe resulting mixture was warmed to room temperature slowly
  6. stirringkept stirring overnight
  7. customThe solvent was removed in vacuo
  8. additionToluene (200 mL) was added
  9. washthe mixture was washed with water (150 mL)
  10. dry with materialdried with Na2SO4
  11. customAfter solvent was removed in vacuo
  12. customthe resulting oil was purified

Sources & evidence

ORD record
ord-01c7b5cfc3c94eb89c2880ee6782851f
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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