Ethyl bromoacetate → (5-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-2-fluoro-phenoxy)-acetic acid ethyl ester

HRID 1095980Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([OH:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:17]([CH3:32])[C:18]([C:24]1[CH:25]=[CH:26][C:27](=[O:31])[N:28]([CH3:30])[CH:29]=1)([OH:23])[C:19]([F:22])([F:21])[F:20].[CH2:33]([O:35][C:36](=[O:39])[CH2:37]Br)[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:33]([O:35][C:36](=[O:39])[CH2:37][O:16][C:11]1[CH:10]=[C:9]([O:8][C:6]2[CH:5]=[CH:4][C:3]([CH:17]([CH3:32])[C:18]([OH:23])([C:24]3[CH:25]=[CH:26][C:27](=[O:31])[N:28]([CH3:30])[CH:29]=3)[C:19]([F:22])([F:20])[F:21])=[C:2]([Cl:1])[CH:7]=2)[CH:14]=[CH:13][C:12]=1[F:15])[CH3:34]

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 10796Cesium carbonate

HCID 574213175-{2-[2-Chloro-4-(4-fluoro-3-hydroxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one

Product 1

HCID 66782632(5-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-phenoxy}-2-fluoro-phenoxy)-acetic acid ethyl ester

Procedure

In analogy to Example 147, step 6, 5-{2-[2-chloro-4-(4-fluoro-3-hydroxy-phenoxy)-phenyl]-1-hydroxy-1-trifluoromethyl-propyl}-1-methyl-1H-pyridin-2-one was reacted with ethylbromoacetate and cesium carbonate to give the title compound as a colorless solid. MS (m/e)=558.2 [M+H+].

Sources & evidence

ORD record: ord-1ecc6fac971d4419a58f9035b20fcf76
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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