[C:1]([C:3]1[CH:4]=C(B(O)O)C=C[CH:8]=1)#N.Br[C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[CH2:21][CH2:20]2)=[N:17][CH:18]=1.Br[C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25]N=1.[Cl-].[CH:31]1([Zn+])[CH2:33][CH2:32]1.[C:35]([O-:38])(O)=[O:36].[Na+].C([O-])([O-])=[O:41].[K+].[K+]>C1COCC1.C1(C)C=CC=CC=1.CCO.O.CCOC(C)=O.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>[C:3]([O:38][C:35](=[O:36])[CH2:25][C:26]([C:27]1[CH:33]=[CH:31][CH:32]=[C:23]([C:13]2[CH:18]=[N:17][C:16]([CH:19]3[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH:28]=1)=[O:41])([CH3:4])([CH3:8])[CH3:1]Compound K7 was obtained from 3-(6-cyclopropyl-pyridin-3-yl)-benzonitrile [prepared by the following procedure: A mixture of 3-cyanophenylboronic acid [CAS-No. 150255-96-2] (8.82 g, 60 mmol), crude 5-bromo-2-cyclopropylpyridine {prepared by the following procedure: A mixture of 2,5-dibromopyridine (11.85 g, 50 mmol), cyclopropyl zinc chloride (0.4 M in THF, 160 mL, 64 mmol), Pd(PPh3)4 (578 mg, 1 mol %) in THF (55 mL) was stirred under Argon atmosphere at 70° C. for 1.5 h. Cooled to RT, poured into sat. NaHCO3-solution, extracted with ether, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown oil (12.36 g).} (ca. 60 mmol), Pd(PPh3)4 (1.733 g, 3 mol %) and K2CO3 (13.82 g, 100 mmol) in toluene (250 mL), EtOH (22 mL) and H2O (50 mL) was stirred at 80° C. for 14 h. Cooled to RT, diluted with EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown solid, which was purified by silica gel column chromatography with cyclohexane/-EtOAc.] (9.88 g, 44.87 mmol) by treatment with tert-butyl bromoacetate and activated zinc, followed by hydrolysis with 10% HCl according to general procedure K (method d).
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