Cesium carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylate

HRID 510715Notes

Reaction equation

HRID 510715 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:34]=[CH:33][C:20]([CH2:21][CH2:22][NH:23][C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=2)=[CH:19][CH:18]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CN1CCCC1=O.Cl[Cu]>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH2:22][NH:23][C:24]([C:25]2[CH:26]=[CH:27][C:28]([O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:8][O:9]4)=[CH:4][CH:3]=3)=[CH:29][CH:30]=2)=[O:32])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 42965003N-(4-chlorophenethyl)-4-iodobenzamideHCID 67080454methyl 7-hydroxy-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 67080596Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylateYield 37.8%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 7-hydroxy-3,4-dihydro-2H-chromene-4-carboxylate (0.075 g, 0.360 mmol), N-(4-chlorophenethyl)-4-iodobenzamide (0.126 g, 0.327 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.00603 g, 0.0327 mmol), CuCl (0.0162 g, 0.164 mmol) and Cs2CO3 (0.213 g, 0.655 mmol) were stirred together in N-methylpyrrolidone (2 mL) at 120° C. for 3 hours. The reaction was cooled and loaded onto a silica gel samplet. The product was a eluted over using a gradient of 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes to provide the title compound (0.056 g, 37.8% yield).

Workup

  1. temperatureThe reaction was cooled
  2. washa eluted

Sources & evidence

ORD record
ord-bfac41e2c395477ca5f9fc0c0bc36b81
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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