Cesium carbonate → HCID 53937827, compound

HRID 2290140Notes

Reaction equation

HRID 2290140 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([NH:16][CH:17]([CH3:19])[CH3:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1)[CH3:21].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]>[CH2:20]([O:22][C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([N:16]([CH:17]([CH3:19])[CH3:18])[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]3[O:12][CH2:11][C:10]([CH3:14])([CH3:15])[C:9]=3[CH:8]=2)=[CH:26][CH:25]=1)[CH3:21]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 634876Binap, (A+-)-HCID 18699171HCID 18699171, compound2×

Product 1

HCID 53937827HCID 53937827, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure E and using 7-t-butyl-3,3-dimethyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 36, 0.63 g, 2.4 mmol), ethyl-4-iodo-benzoate (0.62 3 g, 2.9 mmol), cesium carbonate (1.12 g, 3.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.025 g, 0.025 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.050 g, 0.079 mmol) in 10 mL of anhydrous toluene, the title compound (0.15 g) contaminated with 67% of 7-t-butyl-3,3-dimethyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 36) was obtained.

Sources & evidence

ORD record
ord-d62c2e4ed33f494ca88f1d518c6d5e4c
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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