Water → 6-phenyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749814ノート

反応式

HRID 1749814 の反応式
Br[C:2]1[N:7]=[C:6]2[N:8](C(=O)C3C=CC=CC=3)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.O.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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>[C:20]1([C:2]2[N:7]=[C:6]3[NH:8][CH:9]=[CH:10][C:5]3=[CH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 150138931-Benzoyl-6-bromo-7-azaindole

生成物 1

HCID 866819996-phenyl-1H-pyrrolo[2,3-b]pyridine収率 80.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
110 °C

実験手順

A solution of 6-bromo-1-benzoyl-1H-pyrrolo[2,3-b]pyridine (0.19 g, 0.64 mmol) obtained in Example A47, Step 1 in 1,2-dimethoxyethane (5.0 mL) was successively added with water (2.0 mL), phenylboronic acid (0.16 g, 0.64 mmol), and sodium carbonate (0.20 g, 1.9 mmol). After the inside of the reaction vessel was replaced with argon, the reaction mixture was added with tetrakis(triphenylphosphine)palladium(0) (0.074 g, 0.064 mmol), and the mixture was stirred overnight at 110° C. in a sealed tube. The reaction mixture was extracted with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5)) to obtain 6-phenyl-1H-pyrrolo[2,3-b]pyridine (0.10 g, 80%).

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (99:1→99:5))

出典と根拠

ORDレコード
ord-f27195ee143543c1adc47b4e689d6dd3
出典データセット
uspto-grants-2015_10
特許番号
US09156827B2

反応ノート

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