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

HRID 1162415Notes

Reaction equation

HRID 1162415 reaction equation
[F-].[Cs+].[C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][C:10]=1[F:11])#[N:4].Cl[C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][N:25]=1)[C:19]([O:21][CH3:22])=[O:20]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][N:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH:8]=[CH:9][C:10]=1[F:11])#[N:4]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 27579643-Cyano-4-fluorophenylboronic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Cesium fluoride and tetrakis(triphenylphosphine)-palladium were added to a 1,2-dimethoxyethane solution of (3-cyano-4-fluorophenyl)boronic acid and methyl 2-chloroisonicotinate, followed by reaction under heating to reflux to obtain methyl 2-(3-cyano-4-fluorophenyl)isonicotinate. F: 257.

Workup

  1. customfollowed by reaction
  2. temperatureunder heating
  3. temperatureto reflux

Sources & evidence

ORD record
ord-5eb402bc56cf4f199ce8318e6f8e8b4f
Source dataset
uspto-grants-2010_10
Patent number
US07820700B2

Reaction notes

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