Cesium carbonate → HCID 15454095, compound

HRID 2290163Notes

Reaction equation

HRID 2290163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([CH3:12])([CH3:11])[O:6][C:5]2([CH3:14])[CH3:13].[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]3[C:8](=[CH:9][CH:10]=2)[C:7]([CH3:12])([CH3:11])[O:6][C:5]3([CH3:14])[CH3:13])=[CH:21][CH:20]=1)[CH3:16]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 18007653HCID 18007653, compound2×

Product 1

HCID 15454095HCID 15454095, compoundYield 85%

Reagents, catalysts & solvents 3

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

Procedure

Following general procedure E and using 5-amino-1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran (Compound 78) (1 g, 4.82 mmol), ethyl-4-iodo-benzoate (1.4 g, 5.07 mmol), cesium carbonate (2.2 g, 6.76 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.030 g, 0.03 mmol), (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.060 g, 0.09 mmol) in 15 mL of anhydrous toluene the title compound (1.38 g, 85%) was obtained as a yellow solid after flash column chromatography using 20% ethyl acetate in hexane as the eluent. 1H NMR (300 MHz, CDCl3): δ 7.94 (d, 2H, J=8.7 Hz), 7.10 (dd, 1H J=1.8, 7.9 Hz), 7.03 (d, 1H, J=8.0 Hz), 6.99 (d, 2H, J=8.7 Hz), 6.89 (d, 1H, J=1.7 Hz), 6.36 (s, 1H), 4.34 (q, 2H, J=7.Hz), 1.52 (s, 6H), 1.51 (s, 6H), 1.37 (t, 3H, J=7.1 Hz).

Sources & evidence

ORD record
ord-e3cb5ab80a244b47bc19f9866d18a13a
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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