Triethylamine → Ethyl(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)acetate

HRID 1778126Notes

Reaction equation

HRID 1778126 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1I.[C:21]([C:23]1[CH:24]=[C:25]([NH:29][C:30]([C:32]2[O:33][CH:34]=[CH:35][C:36]=2[CH3:37])=[O:31])[CH:26]=[CH:27][CH:28]=1)#[CH:22].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][S:11]([CH3:13])(=[N:10][C:8]([C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[C:3]([C:22]#[C:21][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30]([C:32]3[O:33][CH:34]=[CH:35][C:36]=3[CH3:37])=[O:31])[CH:24]=2)[CH:4]=1)=[O:9])=[O:12])[CH3:19]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 51337833N-(3-ethynylphenyl)-3-methylfuran-2-carboxamideHCID 118152573Ethyl {N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}acetate

Product 1

HCID 118152579Ethyl(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)acetateYield 47%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl {N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}acetate, (24 mg, 0.06 mmol), 3-methyl-furan-2-carboxylic acid (3-ethynyl-phenyl)-amide (20 mg, 1.5 eq), bis(triphenylphosphine)palladium(II) dichloride (4.1 mg, 0.1 eq), and triphenyl phosphine (0.4 mg, 0.025 eq) in anhydrous DMF (0.5 mL) under a nitrogen atmosphere was added triethylamine (0.05 mL, 5 eq) followed by the addition of copper(I) iodide (2.2 mg, 0.2 eq). The reaction mixture was stirred at RT for 15 minutes and then poured into saturated aq NaHCO3 and extracted with EtOAc (1×). The organic extract was washed with brine (1×) and dried over anhydrous Na2SO4. The organic phase was filtered and concentrated. The residue was purified by chromatography (EtOAc-Hexanes 1:4 to EtOAc). The product containing fractions were combined and concentrated to give the title compound (14 mg, 47%).

Workup

  1. extractionextracted with EtOAc (1×)
  2. extractionThe organic extract
  3. washwas washed with brine (1×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe organic phase was filtered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc-Hexanes 1:4 to EtOAc)
  8. additionThe product containing fractions
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-085904a152cd4d77854f046f28637660
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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