Sodium Bicarbonate → HCID 57843282, compound

HRID 734976Notes

Reaction equation

HRID 734976 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C:13]3=[O:25])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[C:36]([NH:40][S:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)(=[O:43])=[O:42])[CH:37]=[N:38][CH:39]=2)O1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[O:25]=[C:13]1[N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:2]([C:34]4[CH:39]=[N:38][CH:37]=[C:36]([NH:40][S:41]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)(=[O:43])=[O:42])[CH:35]=4)=[CH:3][CH:4]=3)[N:9]=2)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 68505932HCID 68505932, compound

Product 1

HCID 57843282HCID 57843282, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A slurry of 1,1-dimethylethyl 4-(7-bromo-2-quinoxalinyl)-3-oxo-1-piperazinecarboxylate (1.30 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (1.35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.10 mmol), in 1,4-dioxane (6 ml) and saturated sodium bicarbonate solution (2 ml) was stirred at 100° C. for 1 hour. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (80% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (150 mg, 22%) as a tan solid. MS(ES)+ m/e 561.1 [M+H]+.

Workup

  1. customseparated the organic layer
  2. custompurified directly on silica by column chromatography (80% ethyl acetate/hexanes)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0c56088ff8f7409083c1d6d601bc37b6
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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