Sodium hydride → [[2-methyl-1-[(1-naphthalenyl)methyl]-1H-indol-4-yl]oxy]acetic acid methyl ester

HRID 581137Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:22])[N:6]2[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>>[CH3:30][O:29][C:27](=[O:28])[CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:22])[N:6]2[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 60984Methyl bromoacetate

HCID 104935294-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

Product 1

HCID 10808411[[2-methyl-1-[(1-naphthalenyl)methyl]-1H-indol-4-yl]oxy]acetic acid methyl esterYield 463.7%

Procedure

Using the procedure described in Example 1, Part E, 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole (796 mg, 2.8 mmol) was treated with 112 mg (2.8 mmol) of 60% NaH/mineral oil and then 0.27 mL (0.27 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane to give 450 mg (45% yield) of [[2-methyl-1-[(1-naphthalenyl)methyl]-1H-indol-4-yl]oxy]acetic acid methyl ester, 167-171° C.

Workup

customThe product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record: ord-a69aa7b2fccc48afbb7b2e9984862d5d
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919810

Reaction notes

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