Potassium Acetate → 6-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid

HRID 12276

반응식

HRID 12276 반응식
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]3[CH:30]=[C:31]([C:34]([F:37])([F:36])[F:35])[CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1.[B:38]1(B2OC(C)(C)C(C)(C)O2)[O:42]C(C)(C)C(C)(C)[O:39]1.C([O-])(=O)C.[K+]>CS(C)=O>[O:16]=[C:5]1[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=[C:2]([B:38]([OH:42])[OH:39])[CH:3]=[C:4]1[C:17]1[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]2[CH:30]=[C:31]([C:34]([F:37])([F:36])[F:35])[CH:32]=[CH:33][C:19]=2[N:18]=1

참가 물질

5

반응물 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 686811376-Chloro-4-[6-trifluormethyl-1-(2-trimethylsilanylethoxymethyl)-1h-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2h-pyridazin-3-one

생성물 1

HCID 686805966-Oxo-5-[6-tri-fluoromethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-1-(2-trimethylsilanylethoxymethyl)-1,6-dihydropyridazine-3-boronic acid

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
95 °C

실험 절차

6-Chloro-4-[6-trifluormethyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one (prepared in analogy to example 15b), bis(pinacolato)diboron, (1,1′-bis(diphenylphosphine)ferrocene)-palladium(II) chloride-dichloromethane complex and potassium acetate are dissolved in DMSO. The solution is degassed with argon and heated at 95° C. for 2.5 hours. The reaction solution is filtered through silica gel, and the latter is washed with dichloromethane. The solvent is removed in a rotary evaporator, and the crude product is purified by RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)). MS (ES+) m/z 585 (M+H).

후처리

  1. customThe solution is degassed with argon
  2. filtrationThe reaction solution is filtered through silica gel
  3. washthe latter is washed with dichloromethane
  4. customThe solvent is removed in a rotary evaporator
  5. customthe crude product is purified by RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

출처 및 근거

ORD 기록
ord-bb9f641574f3407fbcc52c5df3b9224e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727989B2

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