Dimethylformamide → HCID 86689557, compound

HRID 1853892Notes

Reaction equation

HRID 1853892 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=[O:17])[C:11]3[S:18][CH:19]=[CH:20][C:10]=3[C:9]=2[C:8]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:23][CH:22]=1)(=O)=O.[CH3:38][N:39](C=O)C>[Cl-].[Zn+2].[Cl-].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].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]>[C:38]([C:7]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=[O:17])[C:11]3[S:18][CH:19]=[CH:20][C:10]=3[C:9]=2[C:8]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:30])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:23][CH:22]=1)#[N:39]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86689558HCID 86689558, compound

Product 1

HCID 86689557HCID 86689557, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3007855ZincchlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A solution of 9-{4-[(tert-butoxycarbonylamino)methyl]phenyl}-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate (176 mg, 0.320 mmol), zinc chloride (75 mg, 0.640 mmol), 1,1′-bis(diphenylphosphino)ferrocene (18 mg, 0.032 mmol), and tris(dibenzylideneacetone)dipalladium(0) (15 mg, 0.016 mmol) in anhydrous DMF (4 mL) was heated at 130° C. for 3 h. The reaction mixture was cooled, quenched with water and the resulting precipitate was filtered and purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (120 mg, 87%) as a brown solid: ESI MS m/z 432 [C24H21N3O3S+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with water
  3. filtrationthe resulting precipitate was filtered
  4. custompurified by column chromatography (silica, methanol/methylene chloride gradient)

Sources & evidence

ORD record
ord-53a53e30afe24925809adf68073572c3
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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