Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → HCID 59251137, 화합물

HRID 218165

반응식

HRID 218165 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4(O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]([O:30][Si](C)(C)C)=[C:27]([CH3:29])[CH3:28]>ClCCCl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:27]([CH3:29])([CH3:28])[C:26]([O:25][CH3:24])=[O:30])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 68706594HCID 68706594, 화합물

생성물 1

HCID 59251137HCID 59251137, 화합물수율 99%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 111,2-Dichloroethane용매

실험 절차

To 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-ol (125 mg, 0.40 mmol) in 5 mL of DCE was added TiCl4 (0.44 mmol; 0.44 mL of 1 M solution in DCM). A precipitate immediately formed. The reaction was concentrated in vacuo to approx 1 mL volume and treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.23 mL, 1.2 mmol) and the reaction became homogeneous and was complete. The reaction was quenched with NaHCO3, extracted 4× EtOAc, and combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography using 25% EtOAc in hexanes to give methyl 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoate (155 mg, 99%). MS found: (M+H)+=397.

후처리

  1. customA precipitate immediately formed
  2. concentrationThe reaction was concentrated in vacuo to approx 1 mL volume
  3. customThe reaction was quenched with NaHCO3
  4. extractionextracted 4× EtOAc
  5. dry with materialwere dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 chromatography

출처 및 근거

ORD 기록
ord-d4a5c1a8103045f8a4c58b27fb70af1d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198311B2

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