tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate → 1-BOC-Indazole-5-boronic acid

HRID 571445

반응식

HRID 571445 반응식
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([B:17]3[O:25]C(C)(C)C(C)(C)[O:18]3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CC(C)=O.O>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([B:17]([OH:25])[OH:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

3

반응물 1

HCID 18525862tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

생성물 1

HCID 674250521-BOC-Indazole-5-boronic acid수율 68%

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

To N-Boc-indazole-5-boronic acid pinacol ester (S46) (390 mg, 1.13 mmol, 1.00 equiv) in acetone/H2O (5.0 mL/5.0 mL) at 23° C. was added NH4OAc (436 mg, 5.65 mmol, 5.00 equiv) and NaIO4 (1.21 g, 5.65 mmol, 5.00 equiv). After stiffing for 48 hr at 23° C., the reaction mixture was concentrated in vacuo to remove acetone. To the residual solution was added EtOAc (5 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2×5 mL). The combined organic phases are washed with brine (10 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 200 mg of the title compound as a colorless solid (68% yield).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove acetone
  3. additionTo the residual solution was added EtOAc (5 mL)
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with EtOAc (2×5 mL)
  6. washThe combined organic phases are washed with brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was triturated with Et2O

출처 및 근거

ORD 기록
ord-90458706fc9e4692b04136d2a565b03b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024093B2

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