Ethyl bromoacetate → HCID 69288789, compound

HRID 1247402Notes

Reaction equation

HRID 1247402 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([O:22][CH2:23][CH3:24])[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[O:11])=[C:4]([F:25])[CH:3]=1.[OH:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.[CH2:36]([O:38][C:39](=[O:42])[CH2:40]Br)[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:36]([O:38][C:39](=[O:42])[CH2:40][O:26][C:27]1[CH:28]=[C:29]([C:2]2[CH:7]=[C:6]([F:8])[C:5]([CH:9]([C:10](=[O:11])[NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=3)[O:22][CH2:23][CH3:24])=[C:4]([F:25])[CH:3]=2)[CH:30]=[CH:31][CH:32]=1)[CH3:37]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 21905252HCID 21905252, compound

Product 1

HCID 69288789HCID 69288789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 247.1, (RS)-2-(4-bromo-2,6-difluoro-phenyl)-N-(4-cyano-benzyl)-2-ethoxy-acetamide (example 248.1) was reacted with 3-hydroxyphenylboronic acid. The product of this reaction was alkylated with ethylbromoacetate and cesiumcarbonate in DMF (analogous to example 16.4) to give (RS)-{4′-[(4-cyano-benzylcarbamoyl)-ethoxy-methyl]-3′,5′-difluoro-biphenyl-3-yloxy}-acetic acid ethyl ester. Colorless oil. MS 509.1 ([M+H]+)

Sources & evidence

ORD record
ord-af5841ac4df34931bd672fbefef01677
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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