Dimethylformamide → HCID 67134551, compound

HRID 527970Notes

Reaction equation

HRID 527970 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[C:13]2[CH:14]=[CH:15]C(OC)=[N:17][C:18]=2[C:19](OS(C(F)(F)F)(=O)=O)=[CH:20][CH:21]=1)=[O:11])[CH3:8].[CH3:32][N:33]([CH:35]=[O:36])[CH3:34]>O.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>[CH2:7]([O:9][C:10]([C:12]1[C:13]2[CH:14]=[CH:15][C:35](=[O:36])[N:33]3[CH2:34][C@H:18]([NH2:17])[C:19](=[CH:20][CH:21]=1)[C:32]=23)=[O:11])[CH3:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86656447HCID 86656447, compound

Product 1

HCID 67134551HCID 67134551, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of vinylboronic anhydride pyridine complex (1:1; 3.81 g) in DMF (240 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (731 mg) and stirred under nitrogen for 20 min. The reaction mixture was sequentially treated with K2CO3 (4.372 g) water (73 mL) and 2-methoxy-8-[[(trifluoromethyl)sulfonyl]oxy]-5-quinoline carboxylic acid ethyl ester (12.0 g; prepared in analogy to the corresponding n-butyl ester described in WO 2006/046552) and further stirred at 85° C. overnight. The reaction mixture was diluted with water and extracted with ether. The org. layer was dried over MgSO4, concentrated to dryness and purified by CC (Hex/EA, 4:1), affording a yellow oil (5.40 g; 66% yield).

Workup

  1. stirringfurther stirred at 85° C. overnight
  2. extractionextracted with ether
  3. dry with materiallayer was dried over MgSO4
  4. concentrationconcentrated to dryness
  5. custompurified by CC (Hex/EA, 4:1)
  6. customaffording a yellow oil (5.40 g; 66% yield)

Sources & evidence

ORD record
ord-d57b091c8f4a46dd9ec534dba60a54a5
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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