A Short Synthesis of the 2‑Bromo‑N,9-dimethyl-6,7,8,9-tetrahydro‑5H‑pyrido[2,3‑b]indol-6-amine Building
Block
Posted on 2019-09-26 - 20:20
A concise
synthesis of pharmaceutically useful (R)-tert-butyl N-(2-bromo-9-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-6-yl)-N-methylcarbamate building block 11 is described. The
racemic intermediate 17 was prepared in a single step
from 2-bromo-6-(1-methylhydrazinyl)pyridine sulfate salt (14) and N,3,3-trimethyl-1,5-dioxaspiro[5.5]undecan-9-amine
hydrochloride salt (16). Chiral separation of racemic
intermediate 17 by diasteromeric salt recrystallization
afforded the diasteromeric salt 18 in 37% yield, which
was Boc-protected to afford building block 11. Thus,
the process for the synthesis and chiral separation by diasteromeric
salt crystallization allowed the synthesis of chiral building block 11 in kilogram quantities in 18% overall yield.
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Sreenivasachary, Nampally; Kroth, Heiko; Benderitter, Pascal; Barth, Wolfgang; Pfeifer, Andrea; Muhs, Andreas (2019). A Short Synthesis of the 2‑Bromo‑N,9-dimethyl-6,7,8,9-tetrahydro‑5H‑pyrido[2,3‑b]indol-6-amine Building
Block. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.9b00222