Water → HCID 56644026, compound

HRID 2040875Notes

Reaction equation

HRID 2040875 reaction equation
[C:1]([C:3]1[CH2:7][C:6]2([CH2:12][CH2:11]N(C3C([N+]([O-])=O)=CC=C(C)N=3)[CH2:9][CH2:8]2)[O:5][N:4]=1)#[CH:2].[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](Cl)=[O:29].C(N(CC)CC)C.[OH2:38].[CH2:39]1[CH2:43][O:42][CH2:41]C1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](=[O:29])[C:2]#[C:1][C:3]1[CH2:7][C:6]2([CH2:8][CH2:9][C:41]3([O:42][CH2:43][CH2:39][O:38]3)[CH2:11][CH2:12]2)[O:5][N:4]=1

Participants

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 57493812HCID 57493812, compound

Product 1

HCID 56644026HCID 56644026, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

A mixture of Compound 11a (60 mg, 0.27 mmol), 2-furoyl chloride (40.2 μl, 0.41 mmol), triethylamine (75.5 μl, 0.54 mmol), bis(triphenylphosphine)palladium(II)dichloride (11.4 mg, 0.016 mmol), CuI (11.4 mg, 0.16 mmol) in 4 mL of anhydrous THF was stirred under nitrogen for 3 h. Afterwards, the reaction mixture was poured into water, extracted with EtOAc. The organic solvent was washed with brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (SP1®TM -Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 5:5) to give 85.5 mg (23.4%) of the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic solvent was washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness in vacuo
  5. customThe crude was purified by automated flash chromatography (SP1®TM -Biotage; gradient Petroleum Ether-EtOAc from 7:3 to 5:5)

Sources & evidence

ORD record
ord-2d65fd60e15647c8bc0acad199d085b1
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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