Sodium hydride → HCID 53821643, compound

HRID 1840937Notes

Reaction equation

HRID 1840937 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.Br[CH2:32][CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1>CN(C=O)C>[CH3:3][O:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:32][CH2:33][O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH:22]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

Product 1

HCID 53821643HCID 53821643, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 0.29 g (7 mmol) of a dispersion of 60% NaH in 10 mL of anhydrous DMF under inert atmosphere, a solution of 1.5 g (4 mmol) of 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester, prepared in Example 1 (part D), in 5 mL of DMF was added. After 30 minutes at room temperature, a solution of 1.09 g (5.2 mmol) of 2-(2-bromoethoxy)tetrahydro-2H-piran in 2 mL of DMF was added. The reaction mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the crude mixture was extracted between water and ethyl acetate. The organic phase was separated, dried and after filtering, the solvent was removed under reduced pressure. The crude mixture was purified by flash chromatography over silica affording 1.3 g (65% of yield) of the desired product.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. extractionthe crude mixture was extracted between water and ethyl acetate
  4. customThe organic phase was separated
  5. customdried
  6. filtrationafter filtering
  7. customthe solvent was removed under reduced pressure
  8. customThe crude mixture was purified by flash chromatography over silica affording 1.3 g (65% of yield) of the desired product

Sources & evidence

ORD record
ord-1dbd1ee8b92a4a87abe9d2df5cf61d89
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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