Cesium carbonate → HCID 15454084, compound

HRID 2290121Notes

Reaction equation

HRID 2290121 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[CH2:15]([O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>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].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>[CH2:15]([O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([NH:1][C:2]2[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]3[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=3[CH:12]=2)=[CH:21][CH:20]=1)[CH3:16]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 15454080HCID 15454080, compound2×

Product 1

HCID 15454084HCID 15454084, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure E and using 5-amino-3,3-dimethyl-7-ethyl-2,3-dihydrobenzofuran (Compound 12, 0.22 g, 1.15 mmol), ethyl-4-iodo-benzoate (0.318 g, 115 mmol), cesium carbonate (0.525 g, 1.61 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol), (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 5 mL of anhydrous toluene, the title compound (0.3 g, 77%) was obtained as a deep yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.88 (d, 2H, J=8.8 Hz), 6.79 (m, 4H), 5.92 (br s, 1H), 4.32 (q, 2H, J=7.2 Hz), 4.25 (s, 2H), 2.59 (q, 2H, J=7.5 Hz), 1.36 (t, 3H, J=7.2 Hz), 1.33 (s, 6H), 1.21 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record
ord-c9ca7b404e4b40bb8af696fed02c4cd0
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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