Potassium Carbonate → 2-[5'-(4-Fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethanol

HRID 1019684Notes

Reaction equation

HRID 1019684 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=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.CC([O-])=O.CC([O-])=O.[Pd+2].O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 666607712-(5'-Bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)ethanol

Product 1

HCID 666608522-[5'-(4-Fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethanol

Reagents, catalysts & solvents 3

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

Procedure

Under an inert atmosphere, 3.60 g (12.62 mmol) of 2-(5′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)ethanol, prepared in step 1.1., 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 are introduced into 20 mL of water. 0.142 g (0.63 mmol) of Pd(OAc)2 is then added. The reaction mixture is refluxed for 24 hours.

Workup

  1. temperatureThe reaction mixture is refluxed for 24 hours

Sources & evidence

ORD record
ord-2dbbc6d0195d4881aab5b49a9e7324a7
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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