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Ethanol → [3-(6-Aminopyridin-3-yl)phenyl]methanol

HRID 1891236
ノート
印刷プレビュー

反応式

HRID 1891236 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[OH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(O)C>C1(C)C=CC=CC=1.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>[NH2:14][C:11]1[N:12]=[CH:13][C:8]([C:21]2[CH:22]=[C:17]([CH2:16][OH:15])[CH:18]=[CH:19][CH:20]=2)=[CH:9][CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

生成物 1

HCID 44232377[3-(6-Aminopyridin-3-yl)phenyl]methanol収率 86.2%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

2.0 g of tetrakis(triphenylphosphine)palladium and 75 ml of a 2M solution of sodium carbonate are added to a round-bottomed flask containing a solution of 5.0 g of 5-bromopyridin-2-ylamine in 140 ml of toluene, 5.7 g of 3-(hydroxymethyl)phenylboronic acid and 70 ml of ethanol degassed beforehand. The mixture is heated at 80° C. for 16 h. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is taken up between water and ethyl acetate. The organic phase is separated, dried and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 4.99 g of compound are obtained.

後処理

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-e1cd0982595a41b5a19da61b6a9c4575
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507520B2

反応ノート

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