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

HRID 1443116
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HRID 1443116 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-75 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ccdd328f3dca4370aebff2b88d4f95aa
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07659401B2

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