Toluene → HCID 178444284, compound

HRID 1591023Notes

Reaction equation

HRID 1591023 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:19][C:20]1[C:25](B(O)O)=[CH:24][CH:23]=[C:22]([F:29])[N:21]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:19][C:20]1[C:25]([C:15]2[CH:16]=[CH:17][C:12]([C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)=[CH:13][CH:14]=2)=[CH:24][CH:23]=[C:22]([F:29])[N:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2762713(2,6-Difluoropyridin-3-yl)boronic acidHCID 178444243HCID 178444243, compound

Product 1

HCID 178444284HCID 178444284, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0,05 M of 4-(trans-4-pentylcyclohexyl)bromobenzene, 0,06 M of 2,6-difluoropyridine-3-boronic acid, 1,25 g of Pd(PPh3)4, 100 ml of toluene, 40 ml of ethanol and 50 ml of 2 M Na2CO3 -solution is heated at 60 ° C under stirring for 2 hours. Customary work-up and recrystallisation from ethanol gives 2,6-difluoro-3-[4-(trans-4-pentylcyclohexyl)phenyl]-pyridine with C 58° N 107° I.

Workup

  1. customCustomary work-up and recrystallisation from ethanol

Sources & evidence

ORD record
ord-59343c2aff284eed88b74ce2cdf19ed3
Source dataset
uspto-grants-1993_04
Patent number
US05205962

Reaction notes

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