Cesium carbonate → HCID 54491022, compound

HRID 2290137Notes

Reaction equation

HRID 2290137 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[C:7]([CH3:16])[C:8]2[O:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]=2[CH:15]=1)([CH3:3])[CH3:2].[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]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]2[CH:6]=[C:7]([CH3:16])[C:8]3[O:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]=3[CH:15]=2)=[CH:23][CH:22]=1)[CH3:18]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 634876Binap, (A+-)-HCID 18699170HCID 18699170, compound2×

Product 1

HCID 54491022HCID 54491022, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Following general procedure E and using 5-(isopropyl)amino-3,3,7-trimethyl-2,3-dihydro-benzofuran (Compound 33, 0.43 g, 1.96 mmol), ethyl-4-iodo-benzoate (0.516 g, 2.4 mmol), cesium carbonate (0.92 g, 2.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.015 g, 0.015 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.030 g, 0.047 mmol) in 8 mL of anhydrous toluene, the title compound (0.1 g), contaminated with 10% of ethyl-4-iodo-benzoate, was obtained. Some 5-(isopropyl)amino-3,3,7-trimethyl-2,3-dihydro-benzofuran (Compound 33, 0.21 g) was recovered. 1H NMR (300 MHz, CDCl3): δ 7.82 (d, 2H, J=9.1 Hz), 6.68 (d, 1H, J=2.3 Hz), 6.66 (d, 1H, J=2.3 Hz), 6.51 (d, 2H, J=9.1 Hz), 4.35-4.27 (m, 3H), 4.31 (s, 2H), 2.22 (s, 3H), 1.35-1.30 (m, 3H), 1.34 (s, 6H), 1.15 (d, 6H, J=6.5 Hz).

Sources & evidence

ORD record
ord-8d5d23e5892e44fcb98eeb3681af7744
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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