Dichloromethane → HCID 22345155, compound

HRID 2232936Notes

Reaction equation

HRID 2232936 reaction equation
Br[C:2]1[C:3]([F:15])=[CH:4][C:5]([F:14])=[C:6]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:7]=1.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>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>[F:14][C:5]1[CH:4]=[C:3]([F:15])[C:2]([C:19]2[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=2)=[CH:7][C:6]=1[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22345213HCID 22345213, compound

Product 1

HCID 22345155HCID 22345155, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

5-Bromo-2,4-difluoro-N,N-dimethyl-benzenesulfonamide (400 mg) and 4-pyridine-boronic acid (165 mg) was dissolved in toluene (5 ml) and abs EtoH (5 ml). To the mixture was then added Na2CO3 (200 mg) and Pd(PPh3)4 (79 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) 298 (M+, 77), 256 (36), 191 (bp), 190 (98), 143 (74).

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-59c2543ddad944bba9ceca3f296f3eb5
Source dataset
uspto-grants-2010_05
Patent number
USRE041315E1

Reaction notes

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