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Cesium fluoride → 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-2-methyl-propionic acid methyl ester

HRID 2266685
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HRID 2266685 반응식
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:20])=[N:15][CH:16]=[C:17](I)[CH:18]=1)[CH3:11].[CH3:21][O:22][C:23](=[O:41])[C:24]([CH3:40])([N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1)[CH3:25].[F-].[Cs+]>COCCOC.O>[CH3:21][O:22][C:23](=[O:41])[C:24]([N:26]1[CH:30]=[C:29]([C:17]2[CH:16]=[N:15][C:14]([NH2:20])=[C:13]([O:12][CH:10]([C:3]3[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[Cl:1])[CH3:11])[CH:18]=2)[CH:28]=[N:27]1)([CH3:40])[CH3:25]
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6

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HCID 25953Cesium fluorideHCID 211113953-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amineHCID 59599416Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate

생성물 1

HCID 595994112-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-2-methyl-propionic acid methyl ester

시약·촉매·용매 2

HCID 962
Water
용매
HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

To a solution of 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-iodo-pyridin-2-ylamine (6.363 g, 14.901 mmol) and 2-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]propionic acid methyl ester (4.6 g, 15.64 mmol) in DME (27 mL) was added a solution of CsF (6.79 g, 44.7 mmol) in water (9.3 mL). The reaction mixture was degassed 3 times with N2. Pd(dppf)CH2Cl2 was added and the reaction mixture was degassed 3 times with N2. The reaction was heated to 120° C. in the microwave (subsequent Pd was added in intervals of 30 minutes until the reaction was complete). Water was added and the reaction was extracted with EtOAc, dried over Na2SO4, and concentrated to give 2-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-2-methyl-propionic acid methyl ester. The crude product was purified by a silica gel column chromatography with a gradient of 25%-50% EtOAc/hexanes to provide 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-2-methyl-propionic acid methyl ester (1.46 g, 21% yield) with a Rf 0.11 (50% EtOAc/hexanes).

후처리

  1. customThe reaction mixture was degassed 3 times with N2
  2. additionPd(dppf)CH2Cl2 was added
  3. customthe reaction mixture was degassed 3 times with N2
  4. additionwas added in intervals of 30 minutes until the reaction
  5. additionWater was added
  6. extractionthe reaction was extracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e3b0a98d79ac4130a85853d7f26dcedc
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07858643B2

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