6-(BENZYLOXY)NICOTINALDEHYDE synthesis
- Product Name:6-(BENZYLOXY)NICOTINALDEHYDE
- CAS Number:635712-99-1
- Molecular formula:C13H11NO2
- Molecular Weight:213.23
83664-33-9
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635712-99-1
General procedure for the synthesis of 6-(benzyloxy)nicotinaldehyde from 2-benzyloxy-5-bromopyridine and N,N-dimethylformamide: n-butyllithium (2.5 M hexane solution, 2.61 mL, 1.05 eq.) was slowly added to a tetrahydrofuran solution (25 mL, -78 °C) of 2-benzyloxy-5-bromopyridine (1.64 g, 6.2 mmol). After 1 hour of reaction at -78 °C, N,N-dimethylformamide (0.97 mL, 2 eq.) was added and stirring was continued at -78 °C for 30 minutes. The reaction mixture was rapidly poured into a stirring 5% aqueous sodium bicarbonate solution (50 mL) and extracted with ether (3 x 50 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude product of 1.16 g (quantitative yield), which could be used in the next reaction without further purification. Mass spectrometry analysis showed a molecular ion peak of 186.34 ([MH]+) for the target compound.
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Yield:635712-99-1 88%
Reaction Conditions:
with silver carbonate in acetonitrile at 20;
Steps:
3.a (a) 6-Benzyloxynicotinaldehyde
Benzyl bromide (500 mg, 2.92 mmol) was added to a mixture of 6-hydroxynicotinaldehyde (300 mg, 2.44 mmol), Ag2C03 (1.0 g, 3.66 mmol) and MeCN (15 mL). The mixture was stirred at rt overnight, filtered and concentrated. The residue was partitioned between H2O and EtOAc and the organic layer was washed with H2O, brine, dried over MgSCU and concentrated. The residue was purified by chromatography to give the sub-title compound (455 mg, 2.14 mmol, 88 %).
References:
WO2019/53427,2019,A1 Location in patent:Page/Page column 49
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