ethyl 4-broMo-6-Methoxy-1,5-naphthyridine-3-carboxylate

A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficientlyc) 4-Bromo-6-methoxy-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 ml_) under argon was stirred efficientlyA suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficiently(c) 4-Bromo-6-methoxy-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid . ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately room temperature - may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmol) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90percent).A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 mL) under argon was stirred efficientlyc) 4-Bromo-6-methoxy-[1.5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4-oxo-1, 4-dihydro-[1, 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately RT-may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmole) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90percent).c) 4-Bromo-6-methoxy-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately RT - may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmole) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90percent).(c) 4-Bromo-6-methoxy-[1, 5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4~oxo-1, 4-dihydro-[1, 5]naphthyridine-3-carboxylic acidethyl ester (74.57 g, 300 mmol) in dry DMF (260 ml) under argon was stirred efficiently* ina water bath (to maintain approximately room temperature - may need slight ice-coolingon a large scale). Phosphorus tribromide (30.0 mL, 316 mmol) was added dropwise over15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected bysuction filtration, washed with water and dried under vacuum over phosphorus pentoxideto give the title compound (83.56 g, 90percent).; c) 4-Bromo-6-methoxy-[1, 5]naphthyridine-3-carboxylic acid ethyl ester; A suspension of 6-methoxy-4-oxo-1, 4-dihydro-[1, 5]naphthyridine-3-carboxylic acidethyl ester (74.57 g, 300 mmole) in dry DMF (260 ml_) under argon was stirred efficiently*in a water bath (to maintain approximately RT - may need slight ice-cooling on a largescale). Phosphorus tribromide (30.0 ml_, 316 mmole) was added dropwise over 15 minand stirring was continued for an additional 30 min. Water (1 L) was added, followed bysaturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the titlecompound (83.56 g, 90percent).c) 4-Bromo-6-methoxy-[1 , 5]naphthyridine-3-carboxylic acid ethyl esterA suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately RT - may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmole) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90percent).A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxyIic acid ethyl ester (74.57 g, 300 mmole) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately RT - may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmole) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90percent).A suspension of 6-methoxy-4-oxo-1 , 4-dihydro-[1 , 5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficientlyA suspension of ethyl 6-methoxy-4-oxo-1 , 4-dihydro-1 , 5-naphthyridine-3- carboxylate (6.3 g, 25.4 mmol) in DMF (20 mL) was stirred under N

Molecular Weight:311.13
XLogP3:2.4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:309.99530
Monoisotopic Mass:309.99530
Topological Polar Surface Area:61.3
Heavy Atom Count:18
Complexity:303
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes