Sodium hydride → HCID 11247939, compound

HRID 1840958Notes

Reaction equation

HRID 1840958 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]([CH3:28])[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]>>[CH2:34]([O:35][CH2:36][CH2:37][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:2])=[O:29])[CH2:14][CH2:15]2)=[CH:20]1)[CH3:33]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 54265543HCID 54265543, compound

Product 1

HCID 11247939HCID 11247939, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 0.068 g (0.172 mmol) of 2-{2-[4-(7-methyl-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester (prepared as in Example 138, part A), 0.010 g (0.26 mmol) of NaH in 60% of mineral oil and 0.023 mL (0.22 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 0.074 g (93% of yield) of the desired product.

Workup

  1. customThis compound was prepared
  2. custompurified by chromatography over silica gel affording 0.074 g (93% of yield) of the desired product

Sources & evidence

ORD record
ord-7ec473a123044f668783e88777e7f521
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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