Potassium Carbonate → HCID 86670993, compound

HRID 515367Notes

Reaction equation

HRID 515367 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH2:3][CH2:2]1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[N:9]=[CH:8][N:7]([CH:4]3[CH2:3][CH2:2][N:1]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([OH:34])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])=[CH:23][CH:24]=4)[CH2:6][CH2:5]3)[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67193440HCID 67193440, compound

Product 1

HCID 86670993HCID 86670993, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Piperidin-4-yl)-1H-benzo[d]imidazol-6-amine (4.62 mmol, 1 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.62 mmol, 1.558 g) and potassium carbonate (9.25 mmol, 1.278 g) were combined and stirred in acetonitrile (25 mL) at room temperature for 3 days. The reaction mixture was concentrated at reduced pressure, taken up in dichloromethane, washed with water and concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane) to afford the title compound (784 mg). MS (ESI) m/z 473.2 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with water
  3. concentrationconcentrated under vacuum
  4. customThe resulting residue was purified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-537dc0e6b4934b90926c6fa01c5dfde6
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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