Toluene → HCID 19380596, compound

HRID 2209401Notes

Reaction equation

HRID 2209401 reaction equation
[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=2)=[C:8]([F:20])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([F:28])[CH:27]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C(O)C>[CH2:1]([C:6]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:14]=[N:15][C:16]([C:24]3[CH:23]=[C:22]([F:21])[CH:27]=[C:26]([F:28])[CH:25]=3)=[N:17][CH:18]=2)=[C:8]([F:20])[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 193806082-Chloro-5-(2,6-difluoro-4-pentylphenyl)pyrimidine

Product 1

HCID 19380596HCID 19380596, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 77 mmol of 1A, 92 mmol of 3,5-difluorophenylboronic acid (prepared from 3,5-difluorobromobenzene by reaction with magnesium and trimethyl borate), 200 ml of toluene, 92 ml of ethanol, 2.4 g of tetrakis[triphenylphosphine]palladium(0) and 125 ml of a 2 molar aqueous sodium carbonate solution is heated at the boil for 16 hours. Customary work-up gives the product, which can be processed further without purification.

Workup

  1. temperatureis heated at the boil for 16 hours
  2. customCustomary work-up gives the product, which
  3. customcan be processed further without purification

Sources & evidence

ORD record
ord-5cf726f1a1834c3dab461aaf984cf3d8
Source dataset
uspto-grants-1995_10
Patent number
US05454975

Reaction notes

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