hydrogen; palladium on activated charcoal in tetrahydrofuran; methanol

hydrogenchloride in tetrahydrofuran

1: 83 percent / DIPEA / CH2Cl2 2: 98 percent / n-BuLi; I2 / tetrahydrofuran / -78 °C 3: 85 percent / n-PrNH2; CuI / Pd(PPh3)4 / Heating 4: 88 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1: 98 percent / n-BuLi; I2 / tetrahydrofuran / -78 °C 2: 85 percent / n-PrNH2; CuI / Pd(PPh3)4 / Heating 3: 88 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1: 85 percent / n-PrNH2; CuI / Pd(PPh3)4 / Heating 2: 88 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1.1: MgCl2; Et3N; CH2O / tetrahydrofuran / Heating 1.2: 55 percent / NaOH; H2O2 / H2O 2.1: 83 percent / DIPEA / CH2Cl2 3.1: 98 percent / n-BuLi; I2 / tetrahydrofuran / -78 °C 4.1: 85 percent / n-PrNH2; CuI / Pd(PPh3)4 / Heating 5.1: 88 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1.1: 5 g / E. coli JM109 (pDTG602); fermentation broth / 2 h / fermentation 2.1: 90 percent / EtN(i-Pr)2 / CH2Cl2 3.1: n-BuLi; B(Oi-Pr)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / -78 °C 3.2: Pd(PPh3)4 / 90 °C / Suzuki-Miyaura coupling 4.1: 95 percent / H2 / Pd/C / methanol / 1551.44 Torr 5.1: 87 percent / HCl / tetrahydrofuran View Scheme

1.1: n-BuLi; B(Oi-Pr)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / -78 °C 1.2: Pd(PPh3)4 / 90 °C / Suzuki-Miyaura coupling 2.1: 95 percent / H2 / Pd/C / methanol / 1551.44 Torr 3.1: 87 percent / HCl / tetrahydrofuran View Scheme

1.1: PPh3 / CH2Cl2 / 0 °C 1.2: n-BuLi / tetrahydrofuran 2.1: n-BuLi; B(Oi-Pr)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / -78 °C 2.2: Pd(PPh3)4 / 90 °C / Suzuki-Miyaura coupling 3.1: 95 percent / H2 / Pd/C / methanol / 1551.44 Torr 4.1: 87 percent / HCl / tetrahydrofuran View Scheme