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Ethyl Acetate → 5'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

HRID 2190570
ノート
印刷プレビュー

反応式

HRID 2190570 の反応式
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[C:11]([CH3:16])[CH:10]=2)=[O:7])=[CH:4][N:3]=1.[NH:19]1[CH2:29][CH2:28][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>O1CCOCC1.O>[CH2:26]([O:25][C:23]([CH:22]1[CH2:28][CH2:29][N:19]([C:2]2[CH:18]=[CH:17][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:14]=[CH:13][C:12]([I:15])=[C:11]([CH3:16])[CH:10]=3)=[CH:4][N:3]=2)[CH2:20][CH2:21]1)=[O:24])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 70770Ethyl 4-piperidinecarboxylate2 回HCID 81531DiisopropylethylamineHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

生成物 1

HCID 593181915'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester収率 45%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
115 °C

実験手順

A solution of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide (500 mg, 1.34 mmol), ethyl isonipecotate (250 mg, 1.61 mmol) and diisopropylethyl amine (0.7 mL, 4.02 mmol) in dioxane (15 mL) was heated at 80° C. in a sealed tube for 18.5 h then at 95° C. for 9 h and then at 115° C. for an additional 24 h. The reaction mixture was then cooled, another portion of ethyl isonipecotate (250 mg, 1.61 mmol) was added and the mixture was stirred at 115° C. for 8 h more. The mixture was then cooled and portioned between EtOAc and water. The EtOAc layer was dried over Na2SO4, filtered and concentrated. The residue was chromatographed with a silica gel column and 10-40% EtOAc in hexanes gradient to afford the product. (300 mg, Yield: 45%). HRMS m/z calcd for C21H24N3O3I [M+H]+: 494.0935. Found: 494.0937.

後処理

  1. waitat 115° C. for an additional 24 h
  2. temperatureThe reaction mixture was then cooled
  3. temperatureThe mixture was then cooled
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed with a silica gel column and 10-40% EtOAc in hexanes gradient
  8. customto afford the product

出典と根拠

ORDレコード
ord-87ed9e38effb4639b238da95000b96a9
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324385B2

反応ノート

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