Dimethylformamide → HCID 148240719, compound

HRID 2275245Notes

Reaction equation

HRID 2275245 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-ylmethoxy]-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-9dc1402cbaff4f25a19a2ac11573df97
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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