Potassium Carbonate → HCID 86671004, compound

HRID 515385Notes

Reaction equation

HRID 515385 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:33]3[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:34][C:30]1[CH:29]=[C:28]2[C:33](=[CH:32][CH:31]=1)[N:25]([CH:22]1[CH2:23][CH2:24][N:19]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=3)[CH2:20][CH2:21]1)[CH:26]=[CH:27]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22611608HCID 22611608, compoundHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86671004HCID 86671004, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (3.07 mmol, 1.033 g), 1-(piperidin-4-yl)-1H-indol-5-amine (3.07 mmol, 0.66 g) and potassium carbonate (9.20 mmol, 1.271 g) were combined in acetonitrile (20 mL) and stirred at room temperature overnight. The reaction mixture was concentrated at reduced pressure. The resulting residue was taken up in dichloromethane and washed with water. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The solvent was removed and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 3% methanol/dichloromethane) to afford the title compound (332 mg).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customThe solvent was removed
  6. customthe resulting residue was purified by silica chromatography (
  7. washeluting with a solvent gradient from dichloromethane to 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-177e6950719149e4a574a765372015c1
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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