(6-bromo-1H-indol-2-yl)methanol

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

Procedure: To a suspension of (6-bromo-1H-indol-2-yl)methanol (696 mg, 3.00 mmol) in THF (25.0 mL) was added MnO2 (3.20 g, 37.0 mmol) at 0° C. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the title compound (371 mg, 55%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 9.86 (s, 1H), 9.07 (br s, 1H), 7.64 (s, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.29 (dd, J=8.5, 1.5 Hz, 1H), 7.24 (d, J=1.0 Hz, 1H). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure

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

Procedure: To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH4 (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0° C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15% aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3×). The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H). The reaction was quenched with water and 15% aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite The filtrate was extracted with EtOAc (3×) The extracts were dried over Na2SO4 filtered concentrated under reduced pressure

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

Procedure: The product from Step 1 (1.87 g, 8.3 mmol) was combined with t-butyldimethylsilyl chloride (1.38 g, 9.1 mmol) and imidazole (734 mg, 10.8 mmol) in DMF (15 mL). The mixture was stirred 2 h at room temperature. The solvents were removed by rotary evaporation under reduced pressure. The resulting residue was partitioned in EtOAc and saturated aqueous ammonium chloride. The organic layer was washed with brine, dried over Na2SO4, concentrated and chromatographed on silica gel (0-15% EtOAC in hexanes) to give the product (2.7 g, 96%). LC-MS 340.2, 342.2 [M+H]+, RT 1.62 min. The solvents were removed by rotary evaporation under reduced pressure The resulting residue was partitioned in EtOAc The organic layer was washed with brine dried over Na2SO4 concentrated chromatographed on silica gel (0-15% EtOAC in hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromo-1H-indole-2-carboxylic acid (2.4 g, 10 mmol) was dissolved in THF (20 mL) and cooled to 0° C. Lithium aluminum hydride (20 mmol, 1 M in THF) was added to the solution via syringe. The mixture was stirred overnight at room temperature. The excess reagent was quenched with the slow addition of aqueous KOH (10 mL, 1 M). The mixture was stirred vigorously for 30 min. The mixture was filtered through Celite. The filtrate was concentrated and chromatographed (0-20% EtOAc in CH2Cl2) to afford the product as a yellow powder (1.87 g, 83%). LC-MS 224.1, 226.1 [M+H]+, RT 1.03 min. The excess reagent was quenched with the slow addition of aqueous KOH (10 mL, 1 M) The mixture was stirred vigorously for 30 min The mixture was filtered through Celite The filtrate was concentrated chromatographed (0-20% EtOAc in CH2Cl2)