Benzylamine → 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one
Reaction equation
NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(=O)O.CC(=O)O.CC(C)(C)[O-].[K+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>O=C1NCCc2cc(NCc3ccccc3)ccc21Participants
6
Conditions
- Temperature
- 130 °C
Procedure
**Repeat 02915-84 but use NO solvent** In a 5 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (6.89 mg, 0.01 mmol) and palladium(II) acetate (2.483 mg, 0.01 mmol) combined to give a tan suspension. potassium tert-butoxide (24.82 mg, 0.22 mmol) was then added last. Placed test tube onto Smith MW* platform. Heated reaction to 70°C for 5 minutes. NO reaction!!! Added DMF (0.5 ml) and reheated reaction to 130°C for 15 mins. Took LCMS - no reaction, only unreacted SM!! Discarded reaction.
Sources & evidence
- ORD record
- ord-4a6bd61cd0ff477baa0ad5e567d741e9
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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