Dimethylformamide → HCID 148240719, compound

HRID 61869Notes

Reaction equation

HRID 61869 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:46])([CH3:45])[C@@H:8]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@@H:9]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]2[C:39](=[CH:40][CH:41]=1)[C:38](=[O:42])[C:22]1[C:23]3[CH:29]=[CH:28][C:27](OS(C(F)(F)F)(=O)=O)=[CH:26][C:24]=3[O:25][C:21]=1[C:20]2([CH3:44])[CH3:43])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[CH3:53][N:54](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([SiH2:5][O:6][C:7]([CH3:45])([CH3:46])[C@@H:8]1[O:12][C:11]([CH3:13])([CH3:14])[O:10][C@@H:9]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]2[C:39](=[CH:40][CH:41]=1)[C:38](=[O:42])[C:22]1[C:23]3[CH:29]=[CH:28][C:27]([C:53]#[N:54])=[CH:26][C:24]=3[O:25][C:21]=1[C:20]2([CH3:44])[CH3:43])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 149435112HCID 149435112, compound

Product 1

HCID 148240719HCID 148240719, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
200 °C

Procedure

Trifluoro-methanesulfonic acid 8-[(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy]-6,6 dimethyl-11-oxo-6,11-dihydro-benzo[b]naphth[2,3-d]furan-3-yl ester (Compound Z14, 24 mg) was dissolved in DMF (0.5 mL), added with zinc (II) cyanide (8.2 mg) and palladium tetrakistriphenylphosphine (2.0 mg), and the mixture was stirred under heating at 200° C. for 20 min with microwave irradiation. To the reaction mixture, ethyl acetate was added and the organic layer was washed with saturated brine. Thereafter, the organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (15 mg).

Workup

  1. washthe organic layer was washed with saturated brine
  2. dry with materialThereafter, the organic layer was dried over magnesium sulfate
  3. customThe residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-313e8f8325d5472482b9f9b3652ee21c
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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