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

HRID 510321ノート

反応式

HRID 510321 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-fcb13a1e9b554d77936514fbb6f5935a
出典データセット
uspto-grants-2015_08
特許番号
US09096586B2

反応ノート

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