Sodium Iodide → HCID 86638554, compound

HRID 1807738Notes

Reaction equation

HRID 1807738 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][N:10]=1)=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.O.C(OCC)(=O)C>[CH2:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([OH:40])([C:32]([F:33])([F:34])[F:35])[C:36]([F:37])([F:38])[F:39])=[CH:29][CH:30]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:11][N:10]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67059653HCID 67059653, compound

Product 1

HCID 86638554HCID 86638554, compoundYield 35.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Butyl-3-(5-(piperazine-1-carbonyl)pyridin-2-yl)urea (45 mg, 0.147 mmol), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (55 mg, 0.162 mmol), potassium carbonate (61 mg, 0.442 mmol) and sodium iodide (4 mg, 0.029 mmol) were stirred together in acetonitrile (1.5 mL) at reflux for 2 hours. After this time the mixture was cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, dried and concentrated under reduced pressure. The residue was purified by silica chromatography eluting with 5% methanol in dichloromethane to give the title compound (29 mg).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica chromatography
  6. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-52a2f1427d734d2cbab192d6174fd851
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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