Triethylamine → (RS)-N-(4-cyano-benzyl)-2-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-2-methoxy-acetamide

HRID 1247396Notes

Reaction equation

HRID 1247396 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9](=[O:22])[CH:10]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=2[F:21])[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].[F:25][C:26]1[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=1.CCN(CC)CC.CCOC(C)=O>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:22])[CH:10]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[C:15]([O:20][C:29]3[CH:33]=[CH:34][C:26]([F:25])=[CH:27][CH:28]=3)[C:14]=2[F:21])[O:11][CH3:12])=[CH:23][CH:24]=1)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 99734-Fluorobenzoic AcidHCID 21905078(RS)-N-(4-Cyano-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-methoxy-acetamide

Product 1

HCID 21905328(RS)-N-(4-cyano-benzyl)-2-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-2-methoxy-acetamideYield 61%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-methoxy-acetamide (370 mg) in 1,2-dichloroethane (10 ml) was added copper(II)acetate (222 mg), 4-fluorobenzoic acid (467 mg) and powdered MS4 Å (2 g). Et3N (563 mg) was added and the mixture was stirred 2 days at rt. The mixture was passed over silica gel eluting with AcOEt. CC (AcOEt/Hept 1:3 to 3:1) yielded 203 mg (61%) of (RS)-N-(4-cyano-benzyl)-2-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-2-methoxy-acetamide. Yellow oil. MS 427.0 ([M+H]+).

Sources & evidence

ORD record
ord-a328d37a690f48968f644bb258995f72
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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