Potassium Carbonate → HCID 59234651, compound

HRID 1697856Notes

Reaction equation

HRID 1697856 reaction equation
Br[C:2]1[C:3](=[O:13])[N:4]([CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[CH:5]=[CH:6][CH:7]=1.[F:14][C:15]1[N:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][CH2:11][CH2:10][CH2:9][CH2:8][N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:18]2[CH:19]=[N:20][C:15]([F:14])=[CH:16][CH:17]=2)[C:3]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 59234646HCID 59234646, compound

Product 1

HCID 59234651HCID 59234651, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in 82% yield using a similar procedure as set out earlier in Prep8 starting from 3-bromo-1-(4-chlorobutyl)-2(1H)-pyridinone (Prep7) (400 mg, 1.51 mmol), (6-fluoro-3-pyridinyl)boronic acid (commercial Alfa Aesar) (426 mg, 3.02 mmol), K2CO3 (627 mg, 4.54 mmol), triphenylphosphine (200 mg, 0.75 mmol) and palladium (II) acetate (68 mg, 0.30 mmol) dissolved in dioxane (5 ml).

Sources & evidence

ORD record
ord-f2b24d33a9f045e2a63ec59a1a50daa0
Source dataset
uspto-grants-2012_04
Patent number
US08163927B2

Reaction notes

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