Cesium carbonate → HCID 54068193, compound

HRID 2290123Notes

Reaction equation

HRID 2290123 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)[CH3:18].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]>[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([NH:1][C:2]2[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]3[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=3[CH:12]=2)=[CH:23][CH:22]=1)[CH3:18]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 634876Binap, (A+-)-HCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran2×

Product 1

HCID 54068193HCID 54068193, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure E and using 5-amino-7-t-butyl-3,3-dimethyl-2,3-dihydrobenzofuran (Compound 14, 0.14 g, 0.47 mmol), ethyl-4-iodo-benzoate (0.0.13 g, 0.57 mmol), cesium carbonate (0.22 g, 0.66 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 4 mL of anhydrous toluene, the title compound (0.15 g, 86%) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.92 (d, 2H, J=8.8 Hz), 6.91(d, 1H, J=2.2 Hz), 6.84(d, 1H, J=2.2 Hz), 6.82(d, 1H, J=8.7 Hz), 6.04 (br s, 1H), 4.34 (q, 2H, J=7.1 Hz), 4.26 (s, 2H), 1.36 (s, 9H), 1.33 (s, 6H), 1.29-1.34(buried t, 3H).

Sources & evidence

ORD record
ord-3808850dd69242a29b04dcc28a860e0a
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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