Ethanol → HCID 66592299、化合物

HRID 1093526ノート

反応式

HRID 1093526 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[CH:3][CH:2]=1.[N:15]1[CH:16]=[C:17](B(O)O)[N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12.CCO.C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1>[N:15]1[CH:16]=[C:17]([C:10]2[CH:9]=[C:8]([NH:7][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH:13]=[CH:12][CH:11]=2)[N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 149586063-BromodiphenylamineHCID 55255075Imidazo[1,2-A]pyridin-3-ylboronic acid

生成物 1

HCID 66592299HCID 66592299、化合物収率 2.3%

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

To 3-Bromodiphenylamine (0.16 g, 0.6 mmol) was added imidazo[1,2-a]pyridine-3-ylboronic acid (0.1 g, 0.6 mmol), tetrakis(triphenylphosphine)palladium (0) (35 mg, 5 mol %), EtOH (0.5 ml), toluene (0.5 ml) and 2M Na2CO3 (0.9 ml). The reaction mixture was heated at 80° C. for 6 h, before being allowed to cool and then partitioned between EtOAc and H2O. The organic fraction was separated, washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography (20%-100% EtOAc/hexane) to afford the product (4 mg). MS: [M+H]+ 286.

後処理

  1. temperatureto cool
  2. custompartitioned between EtOAc and H2O
  3. customThe organic fraction was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by silica column chromatography (20%-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-828f594dab914ccaa3106d82b3e6b819
出典データセット
uspto-grants-2012_03
特許番号
US08131527B1

反応ノート

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