Cesium carbonate → 4-[(3,3-Dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[CH2:16]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1)[CH3:17].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]>[CH2:16]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([NH:1][C:2]2[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]3[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=3[CH:12]=2)=[CH:22][CH:21]=1)[CH3:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Following general procedure E and using 5-amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran (Compound 13, 0.085 g, 0.5 mmol), ethyl-4-iodo-benzoate (0.123 g, 0.5 mmol), cesium carbonate (0.228 g, 0.7 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 2 mL of anhydrous toluene (reacted in a sealed tube), the title compound (0.107 g, 76%) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.89(d, 2H, J=8.8 Hz), 6.85 (d, 1H, J=2.0 Hz), 6.80 (d, 1H, J=2.0 Hz), 6.78 (d, 2H, J=8.8 Hz), 5.84 (br s, 1H), 4.32 (q, 2H, J=7.2 Hz), 4.25 (s, 2H), 3.08 (heptet, 1H, J=6.9 Hz), 1.36 (t, 3H, J=7.2 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=6.9 Hz).
Sources & evidence
- ORD record
- ord-5968167ecc474747a3e15f4ce9c4e23f
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093838
Reaction notes
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