Dimethylformamide → HCID 86761662, compound

HRID 1875225Notes

Reaction equation

HRID 1875225 reaction equation
CC[Mg+].[Br-].[Br:5][C:6]1[N:7]=[C:8]([CH2:20][O:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=1Br.CN([CH:35]=[O:36])C>C(OCC)C.C1COCC1>[Br:5][C:6]1[N:7]=[C:8]([CH2:20][O:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=1[CH:35]=[O:36]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70937192HCID 70937192, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 86761662HCID 86761662, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3N EtMgBr (0.086 mL of a 3N solution in diethyl ether, 0.26 mmol) was added to a solution of 4,5-dibromo-2-{[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]methyl}-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (0.12 g, 0.21 mmol) in THF (2 mL). The reaction mixture was stirred for 3 h, DMF was added (0.5 mL, 4.9 mmol), and stirring was continued overnight. The solution was quenched by addition of sat'd NH4Cl and extracted with EtOAc and CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (0-30% EtOAc/hex) to afford the title compound (0.073 g, 69%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.77 (s, 1H), 5.84 (s, 2H), 5.27-5.47 (m, 1H), 4.60-4.77 (m, 1H), 3.74 (ddd, J=9.16, 4.85, 4.67 Hz, 2H), 3.47-3.62 (m, 4H), 0.83-0.95 (m, 11H), 0.04 (s, 6H), −0.06-0.01 (m, 9H).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe solution was quenched by addition of sat'd NH4Cl
  4. extractionextracted with EtOAc and CH2Cl2
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. custompurified by silica gel chromatography (0-30% EtOAc/hex)

Sources & evidence

ORD record
ord-91501b69808b48de9d2c180d8dc92f91
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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