Cesium carbonate → 4-[Isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester
Reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]2[CH:7]=[C:8]([NH:14][CH:15]([CH3:17])[CH3:16])[CH:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:5]=2[O:4][CH2:3]1.[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1)[CH3:20].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]>[CH2:19]([O:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([N:14]([CH:15]([CH3:17])[CH3:16])[C:8]2[CH:9]=[C:10]([CH:11]([CH3:12])[CH3:13])[C:5]3[O:4][CH2:3][C:2]([CH3:1])([CH3:18])[C:6]=3[CH:7]=2)=[CH:25][CH:24]=1)[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Following general procedure E and using 3,3-dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 35, 0.21 g, 0.86 mmol), ethyl-4-iodo-benzoate (0.0.29 g, 1.03 mmol), cesium carbonate (0.39 g, 1.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.020 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.04 g, 0.064 mmol) in 6 mL of anhydrous toluene, the title compound (0.027 g) was obtained; some of the product was eluted as a mixture with the starting amine. Some 5-(isopropyl)amino-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 35) was also recovered. 1H NMR (300 MHz, CDCl3): δ 7.82 (d, 2H, J=9.2 Hz), 6.72 (d, 1H, J=2.0 Hz), 6.64 (d, 1H, J=2.0 Hz), 6.50 (d, 2H, J=9.0 Hz), 4.40-4.26 (m, 5H), 3.10 (heptet, 1H, J=7.0 Hz), 1.34 (t, 3H, J=7.1 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=7.0 Hz), 1.15 (d, 6H, J=6.5 Hz).
Sources & evidence
- ORD record
- ord-05467bb11c6e470fa608ab3a9670c865
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093838
Reaction notes
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