1-Bromopentane → HCID 66815484, compound

HRID 1944532Notes

Reaction equation

HRID 1944532 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH3:13][O:12][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:2]=[CH:3]2)=[O:11]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 66815484HCID 66815484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl indole-5-carboxylate (0.875 g, 5.0 mmol) was added to a suspension of sodium hydride (60% in oil, 0.22 g, 5.5 mmol) in N,N-dimethylformamide (15 mL) at 0° C. The resultant solution was stirred at room temperature for 30 min. Bromopentane (0.706 mL, 5.69 mmol) was added to the solution, and stirring was continued for 4 hours. The solution was poured into ice water (100 mL), and the product was extracted into dichloromethane. The organic solution was washed several times with water and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash silica gel chromatography using 5% ethyl acetate in hexane as the eluant, to give the product, 0.975 g (79%), as an oil. MS: m/z 280 (MH+). 1H NMR (CDCl3): 0.87 (t, 3 H), 1.22-1.40 (m, 4 H), 1.77-1.87 (m, 2 H), 3.92 (s, 3 H), 4.11 (t, 2 H), 6.58 (d, 1 H), 7.14 (d, 1 H), 7.32 (d, 1 H), 7.90 (d of d, 1 H) and 8.40 (d, 1 H).

Workup

  1. extractionthe product was extracted into dichloromethane
  2. washThe organic solution was washed several times with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by flash silica gel chromatography
  6. customto give the product, 0.975 g (79%)

Sources & evidence

ORD record
ord-f23df4281fe748a4926059612e308192
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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