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Dichloromethane → 2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine

HRID 1481554
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HRID 1481554 반응식
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([NH2:19])[CH:13]=[C:12](Cl)[N:11]=1)([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.CCOC(C)=O.O>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([NH2:19])[CH:13]=[C:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([F:35])([F:34])[F:23])[N:11]=1)([CH3:4])([CH3:3])[CH3:2]
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HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 866574152-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-chloro-3-nitro-pyridin-4-ylamine

생성물 1

HCID 674124792-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine

시약·촉매·용매 3

HCID 962Water용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

To a mixture of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-chloro-3-nitro-pyridin-4-ylamine (1.20 g, 3.45 mmol, prepared as described in the previous step), 2-trifluoromethyl-phenyl-boronic acid (786 mg, 4.14 mmol), Cs2CO3 (2.81 g, 8.62 mmol) and Pd(dppf)2.DCM (282 mg, 0.345 mmol) in 1,4-dioxane (12 mL) was added water (5 mL). The resulting mixture was stirred at 110° C. under microwave irradiation for 2 h and then cooled to room temperature. The resulting mixture was treated with of EtOAc (50 mL), then washed with H2O and brine and was dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5:95-40:60 EtOAc-hexanes) yielded 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine as a light brown solid. 1H-NMR (400 MHz, CDCl3) δ: 7.76 (d, J=7.8 Hz, 1H), 7.51-7.65 (m, 2H), 7.46 (d, J=7.3 Hz, 1H), 6.41 (s, 1H), 6.08 (br. s., 2H), 4.50 (t, J=5.3 Hz, 2H), 3.95 (t, J=5.3 Hz, 2H), 0.89 (s, 9H), 0.07 (s, 6H). Mass Spectrum (LCMS, ESI pos.) Calculated For C20H26F3N3O4Si: 458.1 (M+H). Measured: 458.0.

후처리

  1. customprepared
  2. temperaturecooled to room temperature
  3. washwashed with H2O and brine
  4. dry with materialwas dried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-90a514850d514faeac849ff86993df23
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409915B2

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