1,2-Dimethoxyethane → 1-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

HRID 573294ノート

反応式

HRID 573294 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:32]=[CH:31][C:12]([O:13][C:14]3[N:22](COCC[Si](C)(C)C)[C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:35]1[C:39]2=[N:40][CH:41]=[CH:42][CH:43]=[C:38]2[N:37]([CH2:44][CH3:45])[N:36]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>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.O>[CH2:44]([N:37]1[C:38]2[C:39](=[N:40][CH:41]=[CH:42][CH:43]=2)[C:35]([C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[NH:22][C:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]4[N:15]=3)=[CH:31][CH:32]=2)=[N:36]1)[CH3:45]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 667278823-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridineHCID 866889692-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridine

生成物 1

HCID 1784630051-Ethyl-3-[4-(3H-imidazo[4,5-b]pyridin-2-yloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine収率 118%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回

実験手順

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridine (100 mg), 3-bromo-1-ethyl-1H-pyrazolo[4,3-b]pyridine (140 mg), Pd(PPh3)4 (7 mg), Na2CO3 (79 mg), DME (5 mL), and water (1 mL) was refluxed overnight under Ar atmosphere. The mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (90 mg).

後処理

  1. temperaturewas refluxed overnight under Ar atmosphere
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  7. customrecrystallized from AcOEt/hexane

出典と根拠

ORDレコード
ord-1f9d26dfb62241e4bf0e2bf9d81ad895
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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