Sodium;3-oxidodioxaborirane;tetrahydrate → 1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-ol

HRID 77454

반응식

HRID 77454 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12](B3OC(C)(C)C(C)(C)O3)=[CH:13][CH:14]=2)[C:9]([C:25]([F:28])([F:27])[F:26])=[N:8]1.B1([O-])O[O:30]1.O.O.O.O.[Na+]>C1COCC1.O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:30])=[CH:13][CH:14]=2)[C:9]([C:25]([F:28])([F:27])[F:26])=[N:8]1

참가 물질

5

반응물 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 866797401-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-indazole

생성물 1

HCID 866797391-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-ol수율 85.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-indazole (415 mg, 1.047 mmol) in THF (4 mL) and water (4.00 mL) was added sodium perborate tetrahydrate (483 mg, 3.14 mmol). The reaction mixture was heated at 50° C. for 2 h. The organic solvents were evaporated, extracted with EtOAc and washed with water and brine solution, then dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography on silica gel using 50% EtOAc/Petroleum Ether to give 1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-ol (255 mg, 85%). 1HNMR 400 MHz, CDCl3: 6 ppm 1.68-1.75 (m, 4H), 2.05-2.17 (m, 2H), 2.46-2.52 (m, 1H), 3.71-3.77 (m, 1H), 3.98-4.01 (m, 1H), 4.89 (s, 1H), 5.74 (dd, J=2.40, 9.00 Hz, 1H), 7.08 (dd, J=2.40, 9.00 Hz, 1H), 7.13 (d, J=0.80 Hz, 1H), 7.59 (d, J=0.40 Hz, 1H).

후처리

  1. customThe organic solvents were evaporated
  2. extractionextracted with EtOAc
  3. washwashed with water and brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel using 50% EtOAc/Petroleum Ether

출처 및 근거

ORD 기록
ord-a635660e8819444e8160d028e25a1ec4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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