# 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
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