Ethanol → HCID 22397820, compound

HRID 2220104Notes

Reaction equation

HRID 2220104 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])[CH:3]=1.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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(Cl)Cl>[F:12][C:11]([F:14])([F:13])[S:8]([C:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 223978261-Bromo-3-((trifluoromethyl)sulfonyl)benzene

Product 1

HCID 22397820HCID 22397820, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-3-trifluoromethylsulfonyl benzene (580 mg) and 4-pyridine-boronic acid (275 mg) was dissolved in toluene (5 ml) and abs EtOH (5 ml). To the mixture was then added Na2CO3 (424 mg) and Pd(PPh3)4 (119 mg) under an atmosphere of Argon. The resulting mixture was heated to 90° C. for 18 h. Then CH2Cl2 was added and the organic phase was washed with water and dried (MgSO4), filtered and evaporated to dryness. The residue was then used without any further purification. (MS m/z (rel. intensity, 70 eV) 287 (M+, 33), 218 (22), 154 (bp), 127 (56), 69 (27).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was then used without any further purification

Sources & evidence

ORD record
ord-ed61aec80f2e4269a12370b7dbccbc88
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Reaction notes

Loading…