Dimethylformamide → HCID 68995057, compound

HRID 657122Notes

Reaction equation

HRID 657122 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([N:26]([CH2:34][C:35]3[N:40]=[CH:39][C:38]4[O:41][CH2:42][CH2:43][O:44][C:37]=4[CH:36]=3)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:21]2)[C:9](=[O:45])[CH:8]=1)(=O)=O.[CH3:48][N:49](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:48]([C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([N:26]([CH2:34][C:35]3[N:40]=[CH:39][C:38]4[O:41][CH2:42][CH2:43][O:44][C:37]=4[CH:36]=3)[C:27](=[O:28])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:24][CH2:25]2)[C:9](=[O:45])[CH:8]=1)#[N:49]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86635360HCID 86635360, compound

Product 1

HCID 68995057HCID 68995057, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

A solution of 1-{2-[4-((2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl){[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}-7-fluoro-2-oxo-1,2-dihydro-4-quinolinyl trifluoromethanesulfonate (0.131 g, 0.19 mmol), zinc cyanide (0.027 g, 0.23 mmol), tris(dibenzylideneacetone)dipalladium (0.017 g, 0.019 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.042 g, 0.076 mmol) in DMF (3 ml) was degassed with argon then heated at 90° C. for 18 h. The mixture was allowed to cool then separated between ethyl acetate and brine. The organics were isolated, dried and concentrated. Chromatography (10 g silica SPE gradient elution with ethyl acetate/methanol 0-3%) provided the title compound (0.062 g, 58%) as a yellow oil.

Workup

  1. temperatureto cool
  2. customthen separated between ethyl acetate and brine
  3. customThe organics were isolated
  4. customdried
  5. concentrationconcentrated
  6. washChromatography (10 g silica SPE gradient elution with ethyl acetate/methanol 0-3%)

Sources & evidence

ORD record
ord-c3795bfc526c4c5184da59de08c69fb6
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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