Hydrochloric Acid → 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

HRID 520560

Reaction equation

HRID 520560 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28].Cl.ClCCl>N1C=CC=CC=1>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6344Dichloromethane2×HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

Product 1

HCID 595647052,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamideYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirred solution of 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (3 g, 12.00 mmol) in pyridine (12 ml), 2,4-difluorobenzenesulfonyl chloride (1.774 ml, 13.19 mmol) was added and the reaction mixture stirred at RT for 2 h. 2 N hydrogen chloride (aq) (20 ml) and dichloromethane (20 ml) were added and the layers separated. The aqueous layer was washed with additional dichloromethane (2×15 ml) and the organic layers combined, dried (hydrophobic frit) and evaporated in vacuo to give a brown oil. There was still some pyridine in the reaction mixture so 2M hydrogen chloride (aq) and dichloromethane (15 ml) were added to extract one more time. The solvent was removed in vacuo to give the title compound as an orange solid (4.3 g).

Workup

  1. customthe layers separated
  2. washThe aqueous layer was washed with additional dichloromethane (2×15 ml)
  3. customdried (hydrophobic frit)
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. additionwere added
  7. extractionto extract one more time
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-923df9c1c378497eb81a3305c86623bb
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Linked notes

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