Sodium hydride → HCID 23444918, compound

HRID 1840953Notes

Reaction equation

HRID 1840953 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[C:24]([Br:29])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1.[H-].[Na+].Br[CH2:34][CH2:35][O:36][CH2:37][CH3:38]>>[Br:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]([CH2:34][CH2:35][O:36][CH2:37][CH3:38])[CH:21]=[C:20]2[CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][O:11][C:5]2[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=2[C:3]([OH:30])=[O:2])[CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 57163879HCID 57163879, compound

Product 1

HCID 23444918HCID 23444918, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 1.6 g (3.3 mmol) of 2-{2-[4-(7-bromo-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-5-methyl-benzoic acid methyl ester (prepared as in Example 138, part A), 0.17 g (4.2 mmol) of NaH in 60% of mineral oil and 0.45 mL (4 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 0.26 g (34% of yield) of the desired product.

Workup

  1. customThis compound was prepared
  2. custompurified by chromatography over silica gel affording 0.26 g (34% of yield) of the desired product

Sources & evidence

ORD record
ord-ebd4f8cffc644bd7a1d739a28c1746e3
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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