Sodium hydride → HCID 9932752, compound

HRID 1840961Notes

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](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[H-].[Na+].[CH:32]1([CH2:35]Br)[CH2:34][CH2:33]1>>[CH:32]1([CH2:35][N:21]2[C:22]3[C:27](=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:19]([CH:16]3[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][O:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:2])=[O:29])[CH2:18][CH2:17]3)=[CH:20]2)[CH2:34][CH2:33]1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 81503Bromomethylcyclopropane

HCID 54084063HCID 54084063, compound

Product 1

HCID 9932752HCID 9932752, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 2 g (5.1 mmol) of 2-{2-[4-(6-fluoro-1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester, 0.51 g (12.8 mmol) of NaH 60% in mineral oil and 0.99 mL (10.2 mmol) of cyclopropylmethyl bromide. The crude mixture was hydrolised following the procedure described in Example 138 (part C) and purified by flash chromatography over silica gel affording 0.32 g (18% of yield) of the desired product.

Workup

customThis compound was prepared
custompurified by flash chromatography over silica gel affording 0.32 g (18% of yield) of the desired product

Sources & evidence

ORD record: ord-dbcbb61ac7d04e95ab8bbdce3856d0a2
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683096B2

Reaction notes

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