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Hydrochloric Acid → (4-Chloro-2-methylthiazolo[4,5-C]pyridin-7-YL)boronic acid

HRID 1443116
ノート
印刷プレビュー

反応式

HRID 1443116 の反応式
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5](I)=[CH:4][N:3]=1.C([O:16][B:17](OC(C)C)[O:18]C(C)C)(C)C.C([Li])CCC.Cl>C1COCC1>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([B:17]([OH:18])[OH:16])=[CH:4][N:3]=1
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

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 768504784-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridineHCID 178418339Butyllithium

生成物 1

HCID 57416436(4-Chloro-2-methylthiazolo[4,5-C]pyridin-7-YL)boronic acid収率 30.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-75 °C

実験手順

4-Chloro-7-iodo-2-methyl-thiazolo[4,5-c]pyridine (Example B) (2.35 g, 7.56 mmol) and triisopropylborate (1.8 ml, 7.94 mmol) were dissolved in 70 ml THF and cooled to −75° C. n-Butyllithium (1.6M in hexane) (5.0 ml, 7.94 mmol) was added drop wise at −70° C. The reaction mixture was stirred for 1 hour at −75° C. and for 1 hour without ice-bath. 10 ml 2N HCl-solution were added and extracted three times with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was crystallized in acetonitrile to get the desired compound as a red solid (520 mg, 30%), MS: m/e=229.2 (M+H+).

後処理

  1. additionwas added drop wise at −70° C
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized in acetonitrile

出典と根拠

ORDレコード
ord-ccdd328f3dca4370aebff2b88d4f95aa
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07659401B2

反応ノート

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