6-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester → 6-(3-Chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester

HRID 2047703ノート

反応式

HRID 2047703 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:9][C:8]([CH3:25])([CH:23]=[CH2:24])[C:7]=2[N:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:9][C:8]([CH2:23][CH3:24])([CH3:25])[C:7]=2[N:6]=1)=[O:4]

参加物

4

反応物 1

HCID 665877906-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester

生成物 1

HCID 665875226-(3-Chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester収率 99.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

The mixture solution of 6-(3-chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester (360 mg, 1 mmol) and 10% palladium on active carbon (120 mg) in methanol (50 mL) was stirred at room temperature under hydrogen (14 psi) for 8 hours. The catalyst was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 6-(3-chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid methyl ester (360 mg, quant.) as a yellow oil. MS (ESI+) [(M+H)+] 363.2.

後処理

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-5215b9cb39f34707824970c553973625
出典データセット
uspto-grants-2013_11
特許番号
US08592594B2

反応ノート

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