Sodium Carbonate → HCID 18446907, compound

HRID 538402Notes

Reaction equation

HRID 538402 reaction equation
[Br:1]Br.[C:3]1([C:9]2[N:10]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:11]1[N:10]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:13][C:12]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 18446904HCID 18446904, compound

Product 1

HCID 18446907HCID 18446907, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.2 mL, 3.8 mmol) was added slowly to a solution of 4-(2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyridine (1.2 g, 3.41 mmol; Example 1, Step 2) in dry DCM at 0° C., followed by saturated aqueous Na2CO3 solution (40 mL). The reaction mixture was then stirred at rt for 16 h. The reaction was then allowed to partition and the layers separated. The aqueous phase was extracted with EtOAc (2×20 mL) and the combined organic phases were dried (Na2SO4). The resulting residue was purified by flash chromatography (SiO2, 100:0-90:10 DCM-MeOH) to furnish 1.06 g (72%) of 4-(5-bromo-2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyridine: 1H NMR (400 MHz, CDCl3) δ 8.62-8.70 (m, 2H), 7.78-8.05 (m, 2H), 7.77-7.86 (m, 2H), 7.45-7.54 (m, 3H), 5.37 (s, 2H), 3.60-3.70 (m, 2H), 0.92-1.02 (m, 2H), 0.003 (s, 9H).

Workup

  1. customto partition
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. customThe resulting residue was purified by flash chromatography (SiO2, 100:0-90:10 DCM-MeOH)

Sources & evidence

ORD record
ord-b1218c5202e9453ca3e8242dbe402929
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

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