Pyridine → 2-chloro-1-phenyl-1H-indole-3-carbaldehyde

HRID 751326

反応式

HRID 751326 の反応式
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

6

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 3147912-chloro-1H-indole-3-carbaldehyde

生成物 1

HCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehyde収率 88%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-chloro-1H-indole-3-carboxaldehyde (5.00 g, 27.8 mmol), phenylboronic acid (6.79 g, 55.6 mmol), cupric acetate (10.11 g, 55.7 mmol), pyridine (4.40 g, 55.7 mmol), triethylamine (5.63 g, 55.6 mmol), 4 Å molecular sieves (15.0 g) dichloromethane (300 mL) is stirred at room temperature for 4 d. The reaction mixture is filtered through a pad of Celite and the filtrate is washed with water, with 2N aq hydrochloric acid, with sat aq sodium bicarbonate, with brine, dried, filtered and concentrated. The residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (4.40 g, 88% yield) as a yellow solid. NMR (CDCl3) 12.30 (1H, s), 8.37 (1H, d), 7.58-7.70 (3H, m), 7.43 (2H, d), 7.23-7.40 (2H, m), 7.10 (1H, d).

後処理

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. washthe filtrate is washed with water, with 2N aq hydrochloric acid, with sat aq sodium bicarbonate, with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography
  7. washeluting with dichloromethane
  8. additionProduct containing fractions
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-f798e9d485b74db1ac5e44f0d0423c48
出典データセット
uspto-grants-2008_07
特許番号
US07405300B2

関連ノート

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