Isopropanol → 4-Nitro-2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazole

HRID 1695710노트

반응식

HRID 1695710 반응식
Br[C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])O.[Na+].C(O)(C)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C.O>[N+:17]([C:4]1[C:5]2[C:9]([CH:10]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([O:26][CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][O:20]4)=[CH:28][CH:29]=3)[CH:3]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2)([O-:19])=[O:18]

참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 50176524-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 582558186-Bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

생성물 1

HCID 582557524-Nitro-2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazole

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

6-Bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (500 mg, 1.53 mmol), Pd(dppf)Cl2 (125 mg, 0.153 mmol), [4-(tetrahydro-2H-pyran-2-yloxy)phenyl]boronic acid (511 mg, 2.3 mmol), saturated sodium hydrogen carbonate (aq) (3 ml) and isopropyl alcohol (12 ml) were added to each of 5 microwave vessels. All 5 reactions were heated at 150° C. for 10 mins in a Biotage microwave. The reaction mixtures were combined and water (250 ml) and ethyl acetate (250 ml) were added. The mixture was filtered and the organic layer collected. The organic layer was washed with water, then brine, dried over magnesium sulphate, filtered and dried in vacuo. The residue was purified using silica gel chromatography, eluting with 0-25% ethyl acetate in cyclohexane. Appropriate fractions were combined and the solvent was removed in vacuo to give the title compound, 2.3 g.

후처리

  1. customThe reaction mixtures
  2. filtrationThe mixture was filtered
  3. customthe organic layer collected
  4. washThe organic layer was washed with water
  5. dry with materialbrine, dried over magnesium sulphate
  6. filtrationfiltered
  7. customdried in vacuo
  8. customThe residue was purified
  9. washeluting with 0-25% ethyl acetate in cyclohexane
  10. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-82f853ec8b684f54ae40b0fe86210e08
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163743B2

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