Sodium hydride → HCID 11329753, compound

HRID 1840954Notes

Reaction equation

HRID 1840954 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[C:23]([Br:28])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[H-].[Na+].Br[CH2:33][CH2:34][O:35][CH2:36][CH3:37]>>[Br:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:22]=1[N:21]([CH2:33][CH2:34][O:35][CH2:36][CH3:37])[CH:20]=[C:19]2[CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:2])=[O:29])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 69893859Methyl 2-[2-[4-(7-bromo-1H-indol-3-yl)-1-piperidinyl]ethoxy]benzoate

Product 1

HCID 11329753HCID 11329753, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 1.4 g (3.1 mmol) of 2-{2-[4-(7-bromo-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester (prepared as in Example 138, part A), 0.16 g (3.7 mmol) of NaH in 60% of mineral oil and 0.42 mL (3.7 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 0.34 g (28% of yield) of the desired product.

Workup

  1. customThis compound was prepared
  2. custompurified by chromatography over silica gel affording 0.34 g (28% of yield) of the desired product

Sources & evidence

ORD record
ord-afa884ad956f4a70ab1088d394274659
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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