Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 66643633、化合物

HRID 1923600ノート

反応式

HRID 1923600 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])=[CH:26][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)=[CH:26][O:25][N:24]=2)=[N:21][CH:22]=1

参加物

5

反応物 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 866472733-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 66643633HCID 66643633、化合物収率 55.4%

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 (1.36 g, 8.63 mmol) in THF (72 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 10.8 mL, 17.27 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-isoxazole-4-carbaldehyde (1.78 g, 8.63 mmol) in THF (26 mL) was added dropwise. After 1 h the reaction mixture was quenched with citric acid solution (5%, 55 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 (1.67 g, 55%) as a light yellow solid. MS: m/e=348.2 [M−H]−.

後処理

  1. customAfter 1 h the reaction mixture was quenched with citric acid solution (5%, 55 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-6fc7042321a643418103ddab87af1d3e
出典データセット
uspto-grants-2012_05
特許番号
US08178522B2

反応ノート

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