Morpholine → N-[4,5-Difluoro-2-(pyridine-3-carbonyl)-phenyl]-4-morpholin-4-yl-benzenesulfonamide

HRID 29541Notes

Reaction equation

HRID 29541 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=2[C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:83]1[CH2:88][CH2:87][O:86][CH2:85][CH2:84]1>CN(C=O)C.[Pd]>[F:19][C:15]1[C:16]([F:18])=[CH:17][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([N:83]3[CH2:88][CH2:87][O:86][CH2:85][CH2:84]3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[C:13]([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH:14]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 22031701Potassium phosphate, tribasic, monohydrateHCID 597887824-Bromo-N-[4,5-difluoro-2-(pyridine-3-carbonyl)-phenyl]-benzenesulfonamide

Product 1

HCID 59788761N-[4,5-Difluoro-2-(pyridine-3-carbonyl)-phenyl]-4-morpholin-4-yl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure for the synthesis of heterocyclyl and heteroaryl substituted phenylsulfonyl derivatives previously described, using 4-Bromo-N-[4,5-difluoro-2-(pyridine-3 -carbonyl)-phenyl]-benzenesulfonamide 0.2 g (0.44 mmol), potassium phosphate tribasic monohydrate 0.607 g (2.64 mmol), rac-2,2′-bis (diphenylphosphino)-1,1′-binaphthyl 0.082 g (0.06 mmol), morpholine 0.30 g (2.2 mmol) and Pd (dba)3 0.06 g (0.06 mmol) in 2 ml DMF. HPLC purification gave yellow title compound.

Workup

  1. customThe title compound was prepared
  2. customHPLC purification

Sources & evidence

ORD record
ord-bdbb7ebc69cd453a828569ddeb141883
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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