Cesium carbonate → HCID 54535106, compound

HRID 2290138Notes

Reaction equation

HRID 2290138 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6]2[CH:7]=[C:8]([NH:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[C:10]([CH2:11][CH3:12])[C:5]=2[O:4][CH2:3]1.[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1)[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([N:13]([CH:14]([CH3:15])[CH3:16])[C:8]2[CH:9]=[C:10]([CH2:11][CH3:12])[C:5]3[O:4][CH2:3][C:2]([CH3:1])([CH3:17])[C:6]=3[CH:7]=2)=[CH:24][CH:23]=1)[CH3:19]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 634876Binap, (A+-)-HCID 18699196HCID 18699196, compound2×

Product 1

HCID 54535106HCID 54535106, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure E and using 3,3-dimethyl-7-ethyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 34, 0.43 g, 1.96 mmol), ethyl-4-iodo-benzoate (0.45 g, 1.93 mmol), cesium carbonate (0.88 g, 2.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.020 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 6 mL of anhydrous toluene, the title compound (0.23 g, 32%) was obtained. This reaction was conducted in a sealed tube for 7 days. Some 3,3-dimethyl-7-ethyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 34) was recovered. 1H NMR (300 MHz, CDCl3): δ 7.82 (d, 2H, J=9.0 Hz), 6.69 (d, 1H, J=2.0 Hz), 6.66 (d, 1H, J=2.0 Hz), 6.51 (d, 2H, J=9.0 Hz), 4.38-4.26 (m, 5H), 2.60 (q, 2H, J=7.5 Hz), 1.33 (t, 3H, J=7.1 Hz), 1.32 (s, 6H), 1.21 (t, 3H, J=7.5 Hz), 1.15 (d, 6H, J=6.5 Hz)

Sources & evidence

ORD record
ord-33e92c8954584fb7b8edb4ff62caf096
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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