Allyltributylstannane → 3-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide

HRID 1349480ノート

反応式

HRID 1349480 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:11]=[C:12](Br)[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].[CH2:34]([Sn](CCCC)(CCCC)CC=C)[CH2:35][CH2:36]C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:11]=[C:12]([C:35]([CH3:36])=[CH2:34])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8]

参加物

5

反応物 2

HCID 90628AllyltributylstannaneHCID 588591313-Benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide

生成物 1

HCID 588591333-Benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide収率 69.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (138 mg) obtained in Example 161, Step 2 in dioxane (2.5 ml) were added tributyl-2-propenyltin (245 mg) and tetrakis(triphenylphosphine)palladium(0) (60 mg), and the mixture was stirred at 100° C. for 4 hr. The solvent was evaporated, toluene was added, and the mixture was concentrated again. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-isopropenyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (89 mg).

後処理

  1. customThe solvent was evaporated
  2. additiontoluene was added
  3. concentrationthe mixture was concentrated again
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

出典と根拠

ORDレコード
ord-d085fe6402f948148e7c87d65a936497
出典データセット
uspto-grants-2007_05
特許番号
US07211572B2

反応ノート

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