Potassium Carbonate → HCID 59234649, compound

HRID 1697857Notes

Reaction equation

HRID 1697857 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:17]2[CH:18]=[CH:19][N:20]=[C:15]([F:14])[CH:16]=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 59234649HCID 59234649, compoundYield 53%

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared in 53% 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 Synchem OHG product list) (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-09a783befc794c5981f38504b1317a45
Source dataset
uspto-grants-2012_04
Patent number
US08163927B2

Reaction notes

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