Trifluoroacetic acid → HCID 59525921, compound

HRID 385717Notes

Reaction equation

HRID 385717 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][N:7]=1)([CH3:5])[C:3]#[N:4].C(C(C1N=CC(B(O)O)=CC=1)(C)C)#N.FC(F)(F)C(O)=O.Br[C:43]1[S:47][C:46]([N+:48]([O-:50])=[O:49])=[C:45]([C:51]([NH2:53])=[O:52])[CH:44]=1>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.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:3]([C:2]([C:6]1[N:7]=[CH:8][C:9]([C:43]2[S:47][C:46]([N+:48]([O-:50])=[O:49])=[C:45]([C:51]([NH2:53])=[O:52])[CH:44]=2)=[CH:10][CH:11]=1)([CH3:1])[CH3:5])#[N:4]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 534029485-Bromo-2-nitrothiophene-3-carboxamide2×HCID 59525975HCID 59525975, compoundHCID 59526282HCID 59526282, compound

Product 1

HCID 59525921HCID 59525921, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-methyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanenitrile and [6-(1-cyano-1-methylethyl)pyridin-3-yl]boronic acid as trifluoroacetic acid salts (260 mg, approx. 0.673 mmol combined), 5-bromo-2-nitrothiophene-3-carboxamide (169 mg, 0.673 mmol) (Intermediate 10 Step 4), and tetrakis(triphenylphosphine)palladium(0) (38.9 mg, 0.034 mmol) were dissolved in fully degassed tetrahydrofuran (2.7 ml) and fully degassed 2 M aqueous sodium carbonate (0.7 ml). The reaction was stirred at 70° C. for 4 hours. It was then allowed to cool to room temperature, taken up in ethyl acetate, and washed with water (2×) and brine (2×). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified via reverse phase HPLC to yield the title compound.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water (2×) and brine (2×)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-dd01bb853594472a9ac1c6cbd4b3f6ad
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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