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

HRID 751326

반응식

HRID 751326 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehyde수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f798e9d485b74db1ac5e44f0d0423c48
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405300B2

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