6-bromo-1H-indole-2-carboxylic acid → (6-Bromo-1H-indol-2-yl)methanol

Temperature

0 °C

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.

1. customThe excess reagent was quenched with the slow addition of aqueous KOH (10 mL, 1 M)
2. stirringThe mixture was stirred vigorously for 30 min
3. filtrationThe mixture was filtered through Celite
4. concentrationThe filtrate was concentrated
5. customchromatographed (0-20% EtOAc in CH2Cl2)

ORD record

ord-ff61c1df12604ed5ac206d42197f0f92

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409905B2