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

HRID 751326

Reaction equation

HRID 751326 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f798e9d485b74db1ac5e44f0d0423c48
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Linked notes

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