(4-fluoro-1H-indol-2-yl)methanamine

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 36 (130 mg, 0.730 mmol) in anhydrous THF (5.0 mL) was added LiAlH4 (138 mg, 3.65 mmol) at 0-5° C. The reaction mixture was heated at 80° C. overnight. After cooling to RT, the mixture was treated with aq. Na2SO4. The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried and concentrated. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc/TEA (10:10:0.5) to afford 40 mg (33%) of (4-fluoro-1H-indol-2-yl)methanamine (38) as a pale yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 11.22 (s, 1H), 7.14 (d, J=8.0 Hz, 1H), 6.97 (m, 1H), 6.70 (m, 1H), 6.28 (s, 1H), 3.82 (s, 2H). LCMS (ESI) m/z: 148.1 [M+H−17]+. After cooling to RT The resulting mixture was extracted with EtOAc (3×10 mL) The combined organic layers were dried concentrated The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc/TEA (10:10:0.5)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 36 (130 mg, 0.730 mmol) in anhydrous THF (5.0 mL) was added LiAlH4 (138 mg, 3.65 mmol) at 0-5° C. The reaction mixture was heated at 80° C. overnight. After cooling to RT, the mixture was treated with aq. Na2SO4. The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried and concentrated. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc/TEA (10:10:0.5) to afford 40 mg (33%) of (4-fluoro-1H-indol-2-yl)methanamine (38) as a pale yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 11.22 (s, 1H), 7.14 (d, J=8.0 Hz, 1H), 6.97 (m, 1H), 6.70 (m, 1H), 6.28 (s, 1H), 3.82 (s, 2H). LCMS (ESI) m/z: 148.1 [M+H−17]+. After cooling to RT The resulting mixture was extracted with EtOAc (3×10 mL) The combined organic layers were dried concentrated The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc/TEA (10:10:0.5)