Propargyl alcohol → HCID 491950, compound

HRID 1841516Notes

Reaction equation

HRID 1841516 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][CH:16]=[CH:15][C:14]=3I)=[O:9])=[CH:4][CH:3]=1.[CH2:24]([OH:27])[C:25]#[CH:26]>C(NCC)C.[Cu](I)I.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:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([CH:26]=[C:25]([CH2:24][OH:27])[N:12]4[CH:11]=2)[CH:15]=[CH:16][CH:17]=3)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 178522926HCID 178522926, compound

Product 1

HCID 491950HCID 491950, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-8-iodo-3-quinolinecarboxamide (prepared according to the general procedure in WO 9932450, 0.53 g), copper iodide (0.11 g), bis(triphenylphosphine)palladium(II) chloride (0.043 g) and propargyl alcohol (0.085 mL) in 20 mL diethylamine is stirred at room temperature for 18 h. The solid in the reaction mixture is filtered, washed with hexanes and dried. The solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (gradient from CH2Cl2 to 3% MeOH/CH2Cl2) affords N-(4-chlorobenzyl)-2-(hydroxymethyl)-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide as a white solid (0.23 g, 52%), m.p. 211-213° C.

Workup

  1. filtrationThe solid in the reaction mixture is filtered
  2. washwashed with hexanes
  3. customdried
  4. dissolutionThe solid is dissolved in CH2Cl2/MeOH
  5. customPurification by chromatography (gradient from CH2Cl2 to 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fdef0c0d7a4144548dc5351828a1fddc
Source dataset
uspto-grants-2004_01
Patent number
US06683181B2

Reaction notes

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