Sodium Carbonate → N-(3-((5-(4-cyanophenyl)thiazol-2-yl)amino)phenyl)methanesulfonamide

HRID 1035833Notes

Reaction equation

HRID 1035833 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)O1.[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>CCCCCC.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>[C:31]([C:30]1[CH:33]=[CH:34][C:27]([C:2]2[S:6][C:5]([NH:7][C:8]3[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=3)=[N:4][CH:3]=2)=[CH:28][CH:29]=1)#[N:32]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27346254-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 86674186N-(3-((5-bromothiazol-2-yl)amino)phenyl)methanesulfonamide

Product 1

HCID 71471997N-(3-((5-(4-cyanophenyl)thiazol-2-yl)amino)phenyl)methanesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N-(3-((5-bromothiazol-2-yl)amino)phenyl)methanesulfonamide 56 (0.159 g, 0.458 mmol), commercially available 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 57 (0.125 g, 0.545 mmol), Lithium chloride (0.038 g, 0.916 mmol) and tetrakis(triphenylphosphine)palladium (0.058 g, 0.05 mmol) in dry and degassed (using argon) 1,4-Dioxane (20 mL) was added aq. Na2CO3 (1M, 0.91 mL, 0.916 mmol). Reaction mixture was degassed again for 2-3 times for 10 minutes and resulting yellow mixture was stirred under argon at 100° C. for 14 hours. Reaction mixture was filtered through a small pad of celite and concentrated. Crude product was MPLC (Biotage) silica column chromatographed using Acetone:Hexane as an eluent to obtain N-(3-((5-(4-cyanophenyl)thiazol-2-yl)amino)phenyl)methanesulfonamide 58 (0.15 g, 89% yield). MS (ES) m/z 371 (M+H+).

Workup

  1. customin dry
  2. customdegassed (using argon) 1,4-Dioxane (20 mL)
  3. customReaction mixture
  4. customwas degassed again for 2-3 times for 10 minutes
  5. customresulting yellow mixture
  6. customReaction mixture
  7. filtrationwas filtered through a small pad of celite
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-32ce15be68bb4a8cbe691c622fa9e14e
Source dataset
uspto-grants-2013_10
Patent number
US08546400B2

Reaction notes

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