Cesium carbonate → Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetate

HRID 453555Notes

Reaction equation

HRID 453555 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[O:13][CH3:14].[Cl:15][C:16]1[CH:33]=[CH:32][C:19]([CH2:20][CH2:21][NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[CH:18][CH:17]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH:22][C:23]([C:24]2[CH:25]=[CH:26][C:27]([O:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=3[O:13][CH3:14])=[CH:28][CH:29]=2)=[O:31])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 85214Methyl 4-hydroxy-3-methoxyphenylacetateHCID 42965003N-(4-chlorophenethyl)-4-iodobenzamide

Product 1

HCID 68464709Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetateYield 44.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 2-(4-hydroxy-3-methoxyphenyl)acetate (0.204 g, 1.04 mmol), N-(4-chlorophenethyl)-4-iodobenzamide (0.200 g, 0.519 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.00956 g, 0.0519 mmol), Cu(I)Cl (0.0257 g, 0.259 mmol) and Cs2CO3 (0.338 g, 1.04 mmol) were stirred together in NMP (2 ml) for 1 hour. The reaction was loaded onto silica gel and the product eluted using a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate/hexanes. Isolated methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetate (0.105 g, 44.6% yield) as a yellow solid.

Workup

  1. washthe product eluted

Sources & evidence

ORD record
ord-3326a71940c646aa8ff2ff234c362c6f
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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