Pyridine → HCID 46912083、化合物

HRID 751359ノート

反応式

HRID 751359 の反応式
[Cl:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH:11]=[O:12].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH:11]=[O:12]

参加物

6

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 469417132-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

生成物 1

HCID 46912083HCID 46912083、化合物収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (70 mg, 0.39 mmol) cupric acetate (140 mg, 0.77 mmol), phenylboronic acid (93 mg, 0.76 mmol), 4A molecular sieve (200 mg), triethylamine (106 μL), pyridine (61 μL) and dichloromethane (5.5 mL) is vigorously stirred at room temperature for 48 hr. The solids are removed by filtration through a pad of Hi-Flo and the filtrate is concentrated. The residue is purified by chromatography eluting with dichloromethane-2% methanol. Product containing fractions are combined and concentrated to give 2-chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (25 mg, 25% yield) as a pale yellow oil.

後処理

  1. customThe solids are removed by filtration through a pad of Hi-Flo
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography
  4. washeluting with dichloromethane-2% methanol
  5. additionProduct containing fractions
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-12742770d80a47f38f6cf36bc820679b
出典データセット
uspto-grants-2008_07
特許番号
US07405300B2

反応ノート

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