Water → HCID 9953303, compound

HRID 1250825Notes

Reaction equation

HRID 1250825 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([O:22][CH2:23][CH2:24][N:12]4[CH:11]=2)[CH:15]=[C:16](I)[CH:17]=3)=[O:9])=[CH:4][CH:3]=1.[CH2:27]([OH:30])[C:28]#[CH:29].O>C(NCC)C.CO.[Cu+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([O:22][CH2:23][CH2:24][N:12]4[CH:11]=2)[CH:15]=[C:16]([C:29]#[C:28][CH2:27][OH:30])[CH:17]=3)=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 962WaterHCID 7859Propargyl alcoholHCID 22636369HCID 22636369, compound

Product 1

HCID 9953303HCID 9953303, compound

Reagents, catalysts & solvents 4

HCID 104815Copper(1+)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 8021DiethylamineSolvent

Procedure

To a mixture of 539 mg of N-(4-chlorobenzyl)-9-iodo-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide of Preparation 10, 78 mg of copper (I) odide, and 30 mg of bis(triphenylphosphine)palladium dichloride in 11 mL of diethylamine, stirred vigorously under argon, is added 82 μL of propargyl alcohol. The mixture is stirred for 18 hours, then diluted with a little methanol and added to 120 mL of stirred water. The precipitated solid is filtered, washed well with water, and dried in vacuo. The solid is then dissolved in chloroform-methanol, and the solution is filtered to remove copper salts and then absorbed onto silica gel. Flash chromatography eluting with 2-6% methanol in dichloromethane provides 217 mg of the title compound.

Workup

  1. filtrationThe precipitated solid is filtered
  2. washwashed well with water
  3. customdried in vacuo
  4. dissolutionThe solid is then dissolved in chloroform-methanol
  5. filtrationthe solution is filtered
  6. customto remove copper salts
  7. customabsorbed onto silica gel
  8. washFlash chromatography eluting with 2-6% methanol in dichloromethane

Sources & evidence

ORD record
ord-1f5cde6eb1e04154a748e9ea9318d5d5
Source dataset
uspto-grants-2002_01
Patent number
US06340680B1

Reaction notes

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