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Nitrogen → 1-(2,3-dihydro-benzofuran-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

HRID 15994
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HRID 15994 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]4[O:19][CH2:18][CH2:17][C:16]=4[CH:20]=3)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:21][N:22]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[N:23]1.C(=O)([O-])[O-].[Na+].[Na+].N#N>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:19]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:8]3[C:6]4=[N:7][C:2]([C:25]5[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=5)=[CH:3][N:4]=[C:5]4[N:10]=[N:9]3)=[CH:20][C:16]=2[CH2:17][CH2:18]1
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참가 물질

7

반응물 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593418446-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

생성물 1

HCID 593417901-(2,3-dihydro-benzofuran-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine수율 24%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
80 °C

실험 절차

To a solution of 6-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (50 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (34 mg, 0.165 mmol), and sodium carbonate (48 mg, 0.45 mmol) in DME/water (4 mL/1 mL) degassed with N2 was added Pd(PPh3)2Cl2 (5 mg, 0.008 mmol). The reaction solution was degassed with N2 again and stirred for 16 hours at 80° C. The reaction mixture was filtered through celite, concentrated, and purified with a reverse-phased preparative HPLC eluting with acetonitrile-water having 0.1% acetic acid to give 1-(2,3-dihydro-benzofuran-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (12 mg, 24% yield).

후처리

  1. customThe reaction solution was degassed with N2 again
  2. filtrationThe reaction mixture was filtered through celite,
  3. concentrationconcentrated
  4. custompurified with a reverse-phased preparative HPLC
  5. washeluting with acetonitrile-water having 0.1% acetic acid

출처 및 근거

ORD 기록
ord-f62c3f5f9af44c268194a6c5eef725fd
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07732604B2

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