Drug-like Molecules

Examples of retrosynthesis on more complex, drug-like molecules.

4-Phenylpyridine (Suzuki coupling product)

SMILES: c1ccc(-c2ccncc2)cc1

This biaryl compound is typically synthesized via Suzuki-Miyaura cross-coupling.

RENKIN's graph-based suzuki_retro rule disconnects the biaryl bond:

c1ccc(-c2ccncc2)cc1
    → Brc1ccccc1 + OB(O)c1ccncc1
    [suzuki_retro]

or

c1ccc(-c2ccncc2)cc1
    → Brc1ccncc1 + OB(O)c1ccccc1
    [suzuki_retro]

Both bromobenzene (Brc1ccccc1) and 4-pyridineboronic acid (OB(O)c1ccncc1) are in the default building block stock.

N-Phenyl-2-aminopyridine (Buchwald-Hartwig product)

SMILES: c1ccc(Nc2ccccn2)cc1

c1ccc(Nc2ccccn2)cc1
    → Brc1ccccn1 + Nc1ccccc1
    [buchwald_hartwig_retro]

• 2-Bromopyridine (Brc1ccccn1) — in stock
• Aniline (Nc1ccccc1) — in stock

4-Fluorobiphenyl

SMILES: Fc1ccc(-c2ccccc2)cc1

RENKIN finds two Suzuki disconnection modes:

1. Fluorine-substituted arene as the bromide partner:

   Fc1ccc(-c2ccccc2)cc1
       → Brc1ccc(F)cc1 + OB(O)c1ccccc1
   

2. Or the reverse:

   Fc1ccc(-c2ccccc2)cc1
       → Brc1ccccc1 + OB(O)c1ccc(F)cc1
   

Paracetamol (Acetaminophen)

SMILES: CC(=O)Nc1ccc(O)cc1

Amide bond disconnection:

CC(=O)Nc1ccc(O)cc1
    → CC(=O)O + Nc1ccc(O)cc1
    [amide_cleavage]

• Acetic acid (CC(=O)O) — in stock
• 4-Aminophenol (Nc1ccc(O)cc1) — in stock

Try More Examples

→ Open Playground

Paste any SMILES into the playground to explore retrosynthetic routes.