2-(1-Methyl-1H-pyrazol-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline → HCID 57843458, compound

HRID 734959Notes

Reaction equation

HRID 734959 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:16]=[N:15][C:14]3[C:9](=[CH:10][C:11](B4OC(C)(C)C(C)(C)O4)=[CH:12][CH:13]=3)[N:8]=2)[CH:4]=[N:3]1.Br[C:27]1[CH:28]=[C:29]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=2[F:44])(=[O:36])=[O:35])[CH:30]=[N:31][CH:32]=1>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[F:44][C:38]1[CH:39]=[C:40]([F:43])[CH:41]=[CH:42][C:37]=1[S:34]([NH:33][C:29]1[CH:30]=[N:31][CH:32]=[C:27]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:15]=[CH:16][C:7]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:8]3)[CH:28]=1)(=[O:36])=[O:35]

Participants

5

Reactant 2

HCID 578432522-(1-Methyl-1H-pyrazol-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalineHCID 57843410HCID 57843410, compound

Product 1

HCID 57843458HCID 57843458, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(1-methyl-1H-pyrazol-4-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (9.22 mmol), N-(5-bromo-3-pyridinyl)-2,4-difluorobenzenesulfonamide (8.13 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.404 mmol) in 2M aqueous sodium carbonate (40 mL) and 1,4-dioxane (40 mL) was heated at 100° C. for 1 h. Upon cooling, the reaction mixture separated into two layers (aqueous and organic). The organic layer was partitioned between ethyl acetate (50 mL) and water (25 mL). The two aqueous layers were then combined and the pH was adjusted to ˜7 with 2N aqueous HCl. A solid precipitated and was filtered away from the solution. The solid was dried in vacuo and then desiccated over P2O5 to afford the title product (2.5 g, 64%). MS(ES)+ m/e 479 [M+H]+.

Workup

  1. temperatureUpon cooling
  2. customthe reaction mixture separated into two layers (aqueous and organic)
  3. customThe organic layer was partitioned between ethyl acetate (50 mL) and water (25 mL)
  4. customA solid precipitated
  5. filtrationwas filtered away from the solution
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-c204ca67171e4782bc633236233670eb
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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