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Triisopropyl borate → 2-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-boronic acid

HRID 902012
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HRID 902012 반응식
Br[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.C([Li])(C)(C)C.[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C>C1COCC1>[CH3:17][C:13]1[N:12]=[C:11]([C:3]2[C:2]([B:23]([OH:28])[OH:24])=[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][N:5]3[N:4]=2)[CH:16]=[CH:15][CH:14]=1
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참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 59700618HCID 59700618, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 597006142-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 3-bromo-2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine (PREP. 17, 0.2 g, 0.69 mmol) in THF (10 mL) is cooled to −78° C. and treated with tert-butyllithium (1.7 M in pentane, 1.6 mL, 2.8 mmol). This solution is stirred for 30 minutes at −78° C., treated with triisopropyl borate (0.39 g, 2.08 mmol), and stirred for 2 hr at −78° C. The reaction is then quenched with 1N HCl and stirred for 30 minutes at room temp. Evaporation leads to the solid crude product that is used without further purification. MS ES+ m/e 253.9 (M+1).

후처리

  1. stirringstirred for 2 hr at −78° C
  2. customThe reaction is then quenched with 1N HCl
  3. stirringstirred for 30 minutes at room temp
  4. customEvaporation
  5. customis used without further purification

출처 및 근거

ORD 기록
ord-039820b98886424c90cfa49c471797a1
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365066B2

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