Potassium Carbonate → HCID 66690529, compound

HRID 2209312Notes

Reaction equation

HRID 2209312 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13]Br)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][N:22]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13][N:22]([CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73759Bis(2-pyridylmethyl)amineHCID 11045489Methyl 3,5-bis(bromomethyl)benzoate

Product 1

HCID 66690529HCID 66690529, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3,5-bis(bromomethyl)-benzoate (500 mg, 1.6 mmol) and di-(2-picolyl)-amine (800 mg, 725 μL, 4 mmol) were dissolved in ACN followed by the addition of dry K2CO3 (1.1 g, 7.9 mmol). The reaction mixture was refluxed overnight under reflux condenser equipped with a CaCl2 tube. The reaction mixture was filtered and filtrate was evaporated under reduced pressure. Yellow residue was purified by flash chromatography (Al2O3 neutral, firstly AcOEt was used to elute impurities and then MeOH/AcOEt=1:9 (v/v)) affording a pure product as a yellow oil. Yield: 850 mg (95%). 1H NMR (500 MHz, CDCl33) δ 8.51 (m, 4H), 7.94 (d, J=1.5 Hz, 2H), 7.70 (s, 1H), 7.61 (m, 8H), 7.12 (m, 4H), 3.92 (s, 3H), 3.81 (s, 8H), 3.73 (s, 4H). 13C NMR (101 MHz, CDCl3) δ 197.9, 167.1, 159.5, 148.9, 139.7, 136.2, 133.8, 130.2, 128.7, 122.8, 121.9, 60.1, 58.2, 52.0. MS (ESI, m/z): calculated: 558.7 observed: 559.5 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureunder reflux condenser
  3. customequipped with a CaCl2 tube
  4. filtrationThe reaction mixture was filtered
  5. customfiltrate was evaporated under reduced pressure
  6. customYellow residue was purified by flash chromatography (Al2O3 neutral, firstly AcOEt
  7. washto elute impurities

Sources & evidence

ORD record
ord-843112a3c11a419ca494bfa6ebbbb21a
Source dataset
uspto-grants-2016_06
Patent number
US09377466B2

Reaction notes

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