Sodium hydride → HCID 23444879, compound

HRID 1840951Notes

Reaction equation

HRID 1840951 reaction equation
C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=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]=[C:27]([O:30][CH3:31])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1)C.[H-].[Na+].Br[CH2:36][CH2:37][O:38][CH2:39][CH3:40]>>[CH2:37]([O:38][CH2:39][CH2:40][N:23]1[C:24]2[C:29](=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:6]3[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=3[C:4]([OH:3])=[O:32])[CH2:16][CH2:17]2)=[CH:22]1)[CH3:36]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 54444009HCID 54444009, compound

Product 1

HCID 23444879HCID 23444879, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 1.4 g (3.2 mmol) of 2-{2-[4-(5-methoxy-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-5-methyl-benzoic acid ethyl ester (prepared as in Example 138, part A), 0.17 g (4.2 mmol) of NaH in 60% of mineral oil and 0.43 mL (3.8 mmol) of bromoethylethyl ether. The crude mixture was hydrolised following the procedure described in Example 138 (part C) and purified by chromatography over silica gel affording 0.470 g (35% of yield) of the desired product.

Workup

  1. customThis compound was prepared
  2. custompurified by chromatography over silica gel affording 0.470 g (35% of yield) of the desired product

Sources & evidence

ORD record
ord-aae1f4e1617a4cc9a1f59c5c730475d8
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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