Toluene → 4-(5-Tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester
Reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]([C:14]1[S:15][C:16]([S:34][CH3:35])=[C:17]([S:19]([C:22]2[CH:27]=[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:25]=[C:24](Br)[CH:23]=2)(=[O:21])=[O:20])[CH:18]=1)=[O:13].[C:36]([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.C(O)C>[CH2:10]([O:11][C:12]([C:14]1[S:15][C:16]([S:34][CH3:35])=[C:17]([S:19]([C:22]2[CH:23]=[C:24]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:25]=[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:27]=2)(=[O:21])=[O:20])[CH:18]=1)=[O:13])[CH3:36]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
The procedure used in Example 1: step d was followed using benzeneboronic acid (42 mg, 0.35 mmol), 4-(3-bromo-5-tert-butoxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 12: step c) (83 mg, 0.17 mmol)), Na2CO3 (2M, 1.4 mL, 2.8 mmol), Pd(PPh3)4 (48 mg, 0.04 mmol), toluene (5.6 mL), and ethanol (2.8 mL). Analogous aqueous workup and SiO2 flash chromatography (20% EtOAc in hexanes) yielded the title compound (55 mg, 65%). 1H-NMR (CDCl3): δ 8.03 (s, 1H), 7.91 (t, 1H, J=1.6 Hz), 7.63 (t, 1H, J=2.0 Hz), 7.57 (m, 2H), 7.47 (m, 2H), 7.41 (m, 2H), 4.33 (q, 2H, J=7.2 Hz), 2.60 (s, 3H), 1.42 (s, 9H), 1.36 (t, 3H, J=7.2 Hz).
Sources & evidence
- ORD record
- ord-b4343ef4b9f2416cb7c9af41026a5576
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138530B2
Reaction notes
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