Potassium Carbonate → HCID 86670997, compound

HRID 515375Notes

Reaction equation

HRID 515375 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([NH2:16])=[CH:13][CH:14]=3)[CH:9]=[N: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:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:4]1[CH2:3][CH2:2][N:1]([CH2:18][C:19]3[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]=3)[CH2:6][CH2:5]1)[N:8]=[CH:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67194676HCID 67194676, compound

Product 1

HCID 86670997HCID 86670997, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Piperidin-4-yl)-1H-indazol-5-amine (4.85 mmol, 1.05 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.85 mmol, 1.636 g) and potassium carbonate (9.71 mmol, 1.342 g) were combined and stirred in acetonitrile (15 mL) at room temperature for 3 days. The reaction mixture was concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane) to afford the title compound (332 mg). MS (ESI) m/z 473.0 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-d3e281d12fa748c486bfbe04c5f12511
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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