Dichloromethane → HCID 22345155, compound

HRID 584091Notes

Reaction equation

HRID 584091 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-28c99f2c3e29434ca5e0da09b2d5a5dd
Source dataset
uspto-grants-2005_08
Patent number
US06924374B2

Reaction notes

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