Dimethylformamide → HCID 68701183, compound

HRID 14504Notes

Reaction equation

HRID 14504 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21](=[O:22])[C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH2:15][CH2:14][O:13]4)[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.[CH3:26][N:27](C)C=O>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-]#N.[Zn+2].[C-]#N>[CH:23]([C:9]1[O:10][C:11]2[C:20]([C:21](=[O:22])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([C:26]#[N:27])=[CH:3][CH:4]=1)=[CH:19][CH:18]=[C:17]1[C:12]=2[O:13][CH2:14][CH2:15][NH:16]1)([CH3:25])[CH3:24]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 167498117-(4-Chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one

Product 1

HCID 68701183HCID 68701183, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
180 °C

Procedure

A mixture of 7-(4-chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one (71.7 mg, 0.202 mmol), tris(dibenzylideneacetone)dipalladium (0) (92.2 mg, 0.101 mmol), 1,1′-bis(diphenylphosphino)ferrocene (112 mg, 0.202 mmol) and zinc cyanide (24 mg, 0.204 mmol) in N,N-dimethylformamide (2.5 ml) is heated at 180° C. for 40 min under microwave irradiation in an Emrys Optimizer instrument (Biotage AB, Uppsala, Sweden). The mixture is filtered through a short pad of Celite, which is then thoroughly washed through with ethyl acetate. The filtrate is washed successively with water and brine. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient) to afford the title compound.

Workup

  1. filtrationThe mixture is filtered through a short pad of Celite, which
  2. washis then thoroughly washed through with ethyl acetate
  3. washThe filtrate is washed successively with water and brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-3ba665b8e1054935a1a2c1ba98a264df
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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