Water → 5-(5-Methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

HRID 1774797ノート

反応式

HRID 1774797 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[NH:16][C:15](=[O:20])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH:7]=[N:6][CH:5]=1.[H-].[Na+].[CH3:24]I.O>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:24])[C:15](=[O:20])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH:7]=[N:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 866791595-(6-Oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester

生成物 1

HCID 866791615-(5-Methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-(6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (430 mg, 1.52 mmol) in THF (15.0 mL) was added 60% NaH (91 mg, 2.28 mmol) at 0° C. and the reaction mixture was stirred at 2-5° C. for 0.5 h before CH3I (0.3 mL, 4.56 mmol) was added. After stirring overnight at RT, it was poured into water (5.0 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-nicotinic acid methyl ester (383.7 mg, 85%) as a light yellow solid. MS: 298.1 (M+H+).

後処理

  1. additionwas added
  2. extractionAfter extraction with EtOAc
  3. washthe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-48cfe1d53ebf4be9b4bcd707349b6283
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

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