Acetonitrile → HCID 86602254, compound

HRID 272656Notes

Reaction equation

HRID 272656 reaction equation
BrC1C=C([C:8]([NH2:25])([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)C=CC=1.N#[C:27][Br:28].[C:29](#[N:31])C>>[Br:28][C:27]1[CH:11]=[CH:10][CH:9]=[CH:8][C:20]=1[C:23]1[N:24]2[C:29]([NH2:31])=[N:25][CH:8]([C:9]3[CH:10]=[CH:11][C:12]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=3)[C:20]2=[N:21][CH:22]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 10476Cyanogen BromideHCID 59837903HCID 59837903, compound

Product 1

HCID 86602254HCID 86602254, compoundYield 38%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-bromophenyl)-1-(imidazol-2-yl)-1-[4-(trifluoromethoxy)phenyl]methylamine (1.67 g, 4.05 mmol) and cyanogen bromide (1.75 g, 16.5 mmol) in acetonitrile is heated at 100° C. in a sealed tube overnight, cooled to room temperature and concentrated. The resultant residue is purified twice by flash chromatography (silica, 96:4:0.5 methylene chloride/methanol/concentrated ammonium hydroxide, then 85:15 to 50:50 hexanes/ethyl acetate as eluent) to afford the title compound as a yellow solid 0.671 g (38% yield), identified by NMR and mass spectral analyses. 1H NMR (500 MHz, CDCl3) δ 7.61 (t, J=1.6 Hz, 1H), 7.53-7.48 (m, 2H), 7.46-7.41 (m, 3H), 7.27-7.22 (m, 4H); ESI MS m/z 437 [C18H12BrF3N4O+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe resultant residue is purified twice by flash chromatography (silica, 96:4:0.5 methylene chloride/methanol/concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-edba8411b1754d5f958683d52c703fb8
Source dataset
uspto-grants-2008_11
Patent number
US07456186B2

Reaction notes

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