Dimethylformamide → HCID 89442827, compound

HRID 1474647Notes

Reaction equation

HRID 1474647 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26]Br)[CH:20]=2)[O:7][C@@H:6]1[CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:41]2[CH:46]=[CH:45][C:44]([C:47]3([CH:50]=[O:51])[CH2:49][CH2:48]3)=[CH:43][CH:42]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:41]3[CH:46]=[CH:45][C:44]([C:47]4([CH:50]=[O:51])[CH2:48][CH2:49]4)=[CH:43][CH:42]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 59593754HCID 59593754, compound2×HCID 88534174HCID 88534174, compound

Product 1

HCID 89442827HCID 89442827, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1.0 g, 1.77 mmol, Intermediate 1), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropane carbaldehyde (762.0 mg, 2.80 mmol), Pd(dppf)Cl2 (76 mg, 0.09 mmol) and sodium carbonate (591.0 mg, 5.58 mmol) under nitrogen atmosphere, was added DMF and H2O (9 mL, 1:1). The reaction mixture was heated at 80° C. for 1 h. After the completion of the reaction as confirmed by TLC, the solution was cooled to r.t and filtered through celite. The solvent was concentrated in vacuo. The crude compound was diluted with ethyl acetate (100 mL). The organic layer was washed with water (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (silica gel, 1:4 EtOAc:Pet ether) to afford the title compound (320 mg, 29%) as a white solid

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe solution was cooled
  3. filtrationfiltered through celite
  4. concentrationThe solvent was concentrated in vacuo
  5. additionThe crude compound was diluted with ethyl acetate (100 mL)
  6. washThe organic layer was washed with water (3×10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude compound was purified by column chromatography (silica gel, 1:4 EtOAc:Pet ether)

Sources & evidence

ORD record
ord-ee377967b3b24b75b834e71a56b6ed2a
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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