Potassium Carbonate → 6-(3-bromophenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 510321노트

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HRID 510321 반응식
Br[C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[Br:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[C:4]3[N:10]([CH3:11])[N:9]=[CH:8][C:5]3=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2734318(3-Bromophenyl)boronic acidHCID 401522616-Bromo-1-methyl-1H-pyrazolo(4,3-b)pyridine

생성물 1

HCID 866998536-(3-bromophenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 6-bromo-1-methyl-1H-pyrazolo[4,3-b]pyridine (120 mg, 0.566 mmol) and 3-bromophenylboronic acid (136 mg, 0.679 mmol) in degassed 1,4-dioxane (6 mL) and water (2 mL) was added K2CO3 (391 mg, 2.83 mmol) and tetrakis(triphenylphosphine)palladium(0) (32 mg, 0.028 mmol). The reaction mixture was heated at 90° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4 and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C13H10BrN3: 288.01 (M+H+); Found: 288.2 (M+H+).

후처리

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude which
  7. customwas purified by chromatographic column

출처 및 근거

ORD 기록
ord-fcb13a1e9b554d77936514fbb6f5935a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096586B2

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