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5-Thiazolecarboxylic acid, 2-methyl- → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid

HRID 1923581
ノート
印刷プレビュー

反応式

HRID 1923581 の反応式
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1.[Li]CCCC.[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]=[O:28])=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1>C1COCC1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]([OH:28])[CH2:1][C:2]3[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=3)=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 988455-Thiazolecarboxylic acid, 2-methyl-HCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 666436562-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 2-methyl-thiazole-5-carboxylic acid (1.15 g, 8.05 mmol) in THF (67 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 10.06 mL, 16.1 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (1.66 g, 8.05 mmol) in THF (24 mL) was added dropwise. After 3 h the reaction mixture was quenched with citric acid solution (5%, 50 mL) then warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, water, dried over sodium sulfate, filtered and concentrated. Purification by trituration (ethyl acetate) afforded the title compound (1.85 g, 66%) as a light yellow solid. MS: m/e=348.2 [M−H]−.

後処理

  1. customAfter 3 h the reaction mixture was quenched with citric acid solution (5%, 50 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine, water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by trituration (ethyl acetate)

出典と根拠

ORDレコード
ord-70c6b216fa2e4510bec1273ad2f673ea
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178522B2

反応ノート

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