2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 66584619, 화합물

HRID 2369015노트

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HRID 2369015 반응식
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][C:34]([F:38])=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[CH:39](B1OC(C)(C)C(C)(C)O1)=[CH2:40]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:38][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][C:28]([C:27]1[CH:26]=[N:25][N:5]3[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:2]([CH:39]=[CH2:40])=[N:3][C:4]=13)=[CH:37]2

참가 물질

6

반응물 2

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86686735HCID 86686735, 화합물

생성물 1

HCID 66584619HCID 66584619, 화합물수율 88.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To 5-chloro-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (2.5 g, 4.4 mmol) in 1,4-Dioxane (50 mL) and 2M Na2CO3 (25 mL) was added vinylboronic acid pinacol ester (0.9 ml, 5.2 mmol), and Pd(PPh3)4 (0.5 g, 0.4 mmol). The reaction mixture was heated at 100° C. for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. Following removal of dioxane under reduced pressure, organics were extracted with CH2Cl2 (4×40 mL, dried (Na2SO4) and concentrated in vacuo. Gradient column chromatography on silica eluting with 20 to 50% EtOAc/hexanes gave 3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5-vinylpyrazolo[1,5-a]pyrimidin-7-amine as a yellow solid (2.2 g, 3.89 mmol, 88%). LC/MS: 3.05 mins, m/z=566.3 (MH+).

후처리

  1. customconsumption of starting material
  2. customremoval of dioxane under reduced pressure
  3. extractionorganics were extracted with CH2Cl2 (4×40 mL
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d54ee2e3ef294b83bc61688c13453925
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703784B2

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