Reaction SMILES: [F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].Cl[C:18]1[N:23]=[C:22]2[S:24][CH:25]=[CH:26][C:21]2=[CH:20][C:19]=1[C@@H:27]([N:29]1C(=O)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]1=[O:39])[CH3:28]>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.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:18]2[N:23]=[C:22]3[S:24][CH:25]=[CH:26][C:21]3=[CH:20][C:19]=2[C@@H:27]([NH:29][C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:11]([OH:12])=[O:14])=[O:39])[CH3:28])[CH:5]=[CH:6][CH:7]=1
Reactant: O=C([O-])[O-]
Reactant: C[C@@H](c1cc2ccsc2nc1Cl)N1C(=O)c2ccccc2C1=O
Reactant: OB(O)c1cccc(F)c1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: [Na+]
Solvent: ClCCl
Product: C[C@H](NC(=O)c1ccccc1C(=O)O)c1cc2ccsc2nc1-c1cccc(F)c1
Temperature: 90 °C

Procedure:
In a 25 mL round-bottomed reaction flask was combined tetrakistriphenylphosphinepalladium(0) (25 mg, 22 μmol), 3-fluorophenylboronic acid (67 mg, 481 μmol), sodium carbonate (232 mg, 2188 μmol), and (S)-2-(1-(6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (150 mg, 438 μmol). The reaction flask was flushed with nitrogen before the addition of 4 mL of 3:1 acetonitrile:water. The reaction was heated to 90° C. for three days, after which time the reaction was not complete. The reaction was worked up by removing the solvent and repartioning between 10 mL dichloromethane and 10 mL water. The dichloromethane layer was separated and extracted with 10 mL of 50% sat. Na2CO3. The pH of the combined aq layers were adjusted to 1 using 20 mL of 1N HCl, forming a white solid. Dichloromethane was added to dissolve the solid and the organic layer was separated off. The aq. layer was extracted twice with 10 mL of dichloromethane and the combined organics were dried over MgSO4, filtered, and concentrated. The crude material was dissolved in 3 mL MeCN and 1 mL water. To this was added 115 mg Na2CO3, 35 mg 3-fluorophenylboronic acid, and 13 mg tetrakis triphenylphosphine. The reaction was heated to 90° C. overnight, then cooled to room temperature and worked up as above. Subjected to column chromatography (DCM:MEOH). To afford 2-(((S)-1-(6-(3-fluorophenyl)thieno[2,3-b]pyridin-5-yl)ethyl)carbamoyl)benzoic acid. The product was then dissolved in 3 mL ethanol and treated with concentrated HCl (118 μL, 1427 μmol). The reaction was heated to 80° C. for 2 days, after which time an additional charge of HCl (118 μL, 1427 μmol) was added and heated at 80° C. for 1 day. The reaction was cooled to rt and diluted with 6 mL of water. The pH of the solution was adjusted to 10 using 1N NaOH. The reaction was extracted with dichloromethane and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was treated with 2 mL of ethanol, forming a suspension. To this suspension was added hydrazine monohydrate (71 μL, 1427 μmol). After stirring at 60° C. for 2 h, the reaction was cooled to rt and diluted with ethyl acetate, filtered, and concentrated. The residue was dissolved in 20 mL of ethyl acetate and washed with 1×3 mL of water, and 1×3 mL of brine, dried over MgSO4, filtered, concentrated to afford crude (1S)-1-(6-(3-fluorophenyl)thieno[2,3-b]pyridin-5-yl)ethanamine. LC/MS (M+1, found=273.0).