N-bromobutanimide → 1-(4-bromo-1-(tetrahydro-pyran-2-yl)-1H-imidazol-2-yl)-2-methyl-propan-2-ol

HRID 2044510Notes

Reaction equation

HRID 2044510 reaction equation
[CH3:1][C:2]([OH:16])([CH3:15])[CH2:3][C:4]1[N:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][N:8]=1.C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C>[Br:24][C:7]1[N:8]=[C:4]([CH2:3][C:2]([CH3:1])([OH:16])[CH3:15])[N:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 582043162-methyl-1-[1-(tetrahydro-pyran-2-yl)-1H-imidazol-2-yl]-propan-2-ol

Product 1

HCID 582043011-(4-bromo-1-(tetrahydro-pyran-2-yl)-1H-imidazol-2-yl)-2-methyl-propan-2-olYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-methyl-1-[1-(tetrahydro-pyran-2-yl)-1H-imidazol-2-yl]-propan-2-ol (1.12 g, 5 mmol) in DMF (10 mL) at −78° C. was added NBS (0.72 g, 4 mmol) in DMF (pre-cooled to −78° C.). The reaction mixture was warmed to r.t. slowly and stirred at r.t. overnight. The solvent was removed under vacuum and purified by neutral Al2O3 column chromatography (CH2Cl2:MeOH=100:1) to give 0.5 gm of 1-[4-bromo-1-(tetrahydro-pyran-2-yl)-1H-imidazol-2-yl]-2-methyl-propan-2-ol (34%). 1H NMR (CDCl3, 400 MHz): δ 7.03 (s, 1H), 5.13 (dd, J=2.6, 9.6 Hz, 1H), 4.05-4.02 (m, 1H), 3.68-3.62 (m, 1H), 2.82 (d, J=12.0 Hz, 2H), 2.01-1.89 (m, 4H), 1.92 (m, 1H), 1.69-1.60 (m, 3H), 1.24 (m, 6H)

Workup

  1. customThe solvent was removed under vacuum
  2. custompurified by neutral Al2O3 column chromatography (CH2Cl2:MeOH=100:1)

Sources & evidence

ORD record
ord-90c5cae631bb47819fc2ad04cc3756e6
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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