Cesium fluoride → Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

HRID 1160814Notes

Reaction equation

HRID 1160814 reaction equation
[F-].[Cs+].[C:3]([C:5]1[CH:6]=[C:7](OB(O)O)[CH:8]=[CH:9][C:10]=1[F:11])#[N:4].Cl[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][N:26]=1)[C:20]([O:22][CH3:23])=[O:21]>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.COCCOC>[C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][N:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:8]=[CH:9][C:10]=1[F:11])#[N:4]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 67078661(3-Cyano-4-fluorophenyl)boric acid

Product 1

HCID 66995083Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Cesium fluoride and tetrakis(triphenylphosphine)palladium were added to a 1,2-dimethoxyethane solution of (3-cyano-4-fluorophenyl)boric acid and methyl 2-chloroisonicotinate, and the mixture was heated under reflux in an argon atmosphere to obtain methyl 2-(3-cyano-4-fluorophenyl)isonicotinate. F: 257.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux in an argon atmosphere

Sources & evidence

ORD record
ord-8cbed3c6f2d648a6b03c7b0b55ae407d
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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