Sodium hydride → HCID 10667804, compound

HRID 3349Notes

Reaction equation

[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:18])[CH:2]=1.[H-].[Na+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>>[CH3:32][O:31][C:29](=[O:30])[CH2:28][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([CH3:18])[N:8]2[CH2:7][C:3]1[CH:4]=[CH:5][C:6]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:1][CH:2]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 60984Methyl bromoacetate

HCID 10495408HCID 10495408, compound

Product 1

HCID 10667804HCID 10667804, compoundYield 125%

Procedure

Using the procedure described in Example 1, Part E, 1-([1,1'-biphenyl]-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole (970 mg, 3.1 mmol) was treated with 124 mg (3.1 mmol) of 60% NaH/mineral oil and then 0.29 mL (3.1 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 747 mg (63% yield) of [[1-([1,1'-biphenyl]-4-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 164°-167° C.

Workup

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

Sources & evidence

ORD record: ord-6e4a7111550b4748814745d936cdc81f
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733923

Reaction notes

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