3-Pyridinecarboxaldehyde → HCID 10881145, compound

HRID 1600173Notes

Reaction equation

HRID 1600173 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[CH:13]=1.C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:18][C:14]1[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 12052TriethylsilaneHCID 50039685-Bromo-2-methylindole

Product 1

HCID 10881145HCID 10881145, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-2-methyl-1H-indole (J. Chem. Soc., 1428 (1965)) (2.0 g) and 3-pyridinecarboxaldehyde (1.02 g) in dry dichloromethane (20 ml) was added dropwise over 10 minutes to a stirred solution of triethylsilane(3.30 g) in trifluoroacetic acid (20 ml) at 0° C. The solution was stirred at 0° C. for 30 minutes and then evaporated under vacuum, keeping the temperature below 35° C. The residue was dissolved in dichloromethane, and the solution was washed with 2N sodium hydroxide, water and dried (MgSO4). The solution was evaporated and the residue was chromatographed on silica gel, using dichloromethane/methanol (50:1) as eluent. The product fractions were combined and evaporated, and the residue was crystallised from ether to give the title compound (2.15 g), m.p. 188°-190° C. Found: C,59.62; H,4.43; N,9.26. C15 H13BrN2 requires: C,59.82; H,4.35; N,9.30%.

Workup

  1. customevaporated under vacuum
  2. customthe temperature below 35° C
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe solution was washed with 2N sodium hydroxide, water
  5. dry with materialdried (MgSO4)
  6. customThe solution was evaporated
  7. customthe residue was chromatographed on silica gel
  8. customevaporated
  9. customthe residue was crystallised from ether

Sources & evidence

ORD record
ord-75f2916e50af49b79d8f15e75eef7ee4
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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