Benzyl Bromide → HCID 54201863, compound

HRID 2292761Notes

Reaction equation

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

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 24758Sodium hydride

HCID 10755860HCID 10755860, compound

Product 1

HCID 54201863HCID 54201863, compoundYield 56.2%

Procedure

Using the procedure described in Example 2, Part B, 2.18 g (7.5 mmol) of 5-ethoxycarbonyl-2-methyl-1H-indole-3-acetic acid ethyl ester was reacted with 320 mg (8 mmol) of 60% NaH/mineral oil and 1.0 mL (8.4 mmol) of benzyl bromide to give after silica chromatography (25% ether/hexane→50% ether/hexane) 1.6 g (56%) of 5-ethoxycarbonyl-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

Sources & evidence

ORD record: ord-63a48da8cdc1482e996ea2b52c5e96ac
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05684034

Reaction notes

Loading…