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Dimethyl-1,3-thiazole-5-carboxylic acid → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid

HRID 1923573
ノート
印刷プレビュー

反応式

HRID 1923573 の反応式
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]=[O:29])=[C:26]([CH3:30])[O:25][N:24]=2)=[N:21][CH:22]=1>C1COCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]([OH:29])[CH2:1][C:2]3[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=3)=[C:26]([CH3:30])[O:25][N:24]=2)=[N:21][CH:22]=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 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 666437052-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
2 回

実験手順

To a stirred solution of 2,4-dimethyl-thiazole-5-carboxylic acid (650 mg, 7.0 mmol) in THF (33 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 4.94 mL, 7.9 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (814 mg, 3.95 mmol) in THF (12 mL) was added dropwise. After 2 h the reaction mixture was quenched with citric acid solution (5%, 25 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 recrystallization (ethyl acetate) afforded the title compound (729 mg, 51%) as a light yellow solid. MS: m/e=362.2 [M+H]+.

後処理

  1. customAfter 2 h the reaction mixture was quenched with citric acid solution (5%, 25 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
  8. customby recrystallization (ethyl acetate)

出典と根拠

ORDレコード
ord-07c00ccfa2b840d5a9a28440a16892b1
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

読み込み中…

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