Potassium Carbonate → HCID 67130432, compound

HRID 1403689Notes

Reaction equation

HRID 1403689 reaction equation
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]3)[CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 21096924HCID 21096924, compound

Product 1

HCID 67130432HCID 67130432, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Under an inert atmosphere, 3.6 g (12.62 mmol) of 2-(6′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)ethanol (WO2004/099176), 3.53 g (25.25 mmol) of 4-fluorophenylboronic acid, 5.23 g (37.87 mmol) of potassium carbonate and 4.88 g (15.15 mmol) of tetrabutylammonium bromide in suspension in 20 ml of water are introduced. Subsequently 0.142 g (0.63 mmol) of Pd(OAc)2 is added. The reaction mixture is subsequently heated at reflux for 24 hours.

Workup

  1. temperatureThe reaction mixture is subsequently heated
  2. temperatureat reflux for 24 hours

Sources & evidence

ORD record
ord-2bf6dcebd8e64af28482d24d70db0e23
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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