Pyridine → HCID 59812087, compound

HRID 2114074Notes

Reaction equation

HRID 2114074 reaction equation
N1C=CC=CC=1.[Br-:7].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:28][N:29]([CH3:53])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[C:38]3[CH:44]=[CH:43][N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:39]3=[N:40][CH:41]=2)=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:7][C:44]1[C:38]2[C:39](=[N:40][CH:41]=[C:36]([C:33]3[CH:34]=[CH:35][C:30]([N:29]([CH3:53])[CH3:28])=[CH:31][CH:32]=3)[CH:37]=2)[N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:51])([CH3:50])[CH3:52])[CH:43]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 21124087PyridiniumtribromideHCID 57830140HCID 57830140, compound

Product 1

HCID 59812087HCID 59812087, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.180 mL, 2.23 mmol) and pyridinium tribromide (0.832 g, 2.34 mmol) were added to a stirred and cooled (−70° C.) solution of 59 (0.820 g, 2.23 mmol) in CH2Cl2 (10 mL). The mixture was stirred at −70° C. for 30 min., poured into saturated aqueous NaHCO3 solution and extracted with CH2Cl2. The organic extract was washed with brine, dried (MgSO4), and concentrated. The residue was purified by means of SGC with hexane:AcOEt as eluent to afford 60 (0.700 g, 70%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.94-1.01 (m, 2H), 3.07 (s, 6H), 3.58-3.64 (m, 2H), 5.71 (s, 2H), 6.88-6.93 (m, 2H), 7.43 (s, 1H), 7.56-7.62 (m, 2H), 8.01 (d, J=0.21 Hz, 1H), 8.62 (d, J=0.21 Hz, 1H).

Workup

  1. stirringThe mixture was stirred at −70° C. for 30 min.
  2. extractionextracted with CH2Cl2
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by means of SGC with hexane

Sources & evidence

ORD record
ord-2c61857ab4ce4bea9188785089e8f3d1
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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