Potassium Carbonate → HCID 57742340, 화합물

HRID 655302노트

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HRID 655302 반응식
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:17]3[N:18]=[CH:19][CH:20]=[N:21][C:16]3=[N:15][N:14]=1)=[CH:7][CH:6]=2.[CH3:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[CH3:22][N:23]1[CH:27]=[C:26]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([CH2:12][C:13]2[N:17]4[N:18]=[CH:19][CH:20]=[N:21][C:16]4=[N:15][N:14]=2)=[CH:7][CH:6]=3)[CH:25]=[N:24]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57742362HCID 57742362, 화합물

생성물 1

HCID 57742340HCID 57742340, 화합물

시약·촉매·용매 1

HCID 962Water용매

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온도
135 °C

실험 절차

A mixture of 3-bromo-6-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl-quinoline (69 mg, 0.204 mmol), 1-methyl-4-pyrazoleboronic acid pinacol ester (51 mg, 0.25 mmol), potassium carbonate (56 mg. 0.41 mml), 1,4-dioxane (2 mL) and water (1 mL) was bubbled nitrogen gas through for 10 minutes. After such time dichlorobis(triphenylphosphine)palladium (8 mg, 5 mol %) was added, the vial sealed and heated in a microwave for 1500 seconds at 135° C. The mixture was diluted with dichloromethane and brine, before the organic phase was concentrated onto silica gel and via flash column chromatography (SiO2 4 g, dichloromethane/CH3OH 0-10%) to return the title compound a white solid (11 mg, 16%). Analytical data presented in Table 2.

후처리

  1. customwas bubbled nitrogen gas through for 10 minutes
  2. additionAfter such time dichlorobis(triphenylphosphine)palladium (8 mg, 5 mol %) was added
  3. customthe vial sealed
  4. additionThe mixture was diluted with dichloromethane and brine, before the organic phase
  5. concentrationwas concentrated onto silica gel and via flash column chromatography (SiO2 4 g, dichloromethane/CH3OH 0-10%)

출처 및 근거

ORD 기록
ord-099c75a48e2d481d8021a2f8294b0e68
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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