Propargyl alcohol → HCID 10180536, compound

HRID 1168539Notes

Reaction equation

HRID 1168539 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:13]=[C:14](I)[CH:15]=[C:16]4[C:21]=3[N:20]([CH:22]=2)[N:19]([CH3:23])[CH2:18][CH2:17]4)=[O:9])=[CH:4][CH:3]=1.[CH2:28]([OH:31])[C:29]#[CH:30].C(NCC)C>>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:13]=[C:14]([C:30]#[C:29][CH2:28][OH:31])[CH:15]=[C:16]4[C:21]=3[N:20]([CH:22]=2)[N:19]([CH3:23])[CH2:18][CH2:17]4)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 12083065HCID 12083065, compound

Product 1

HCID 10180536HCID 10180536, compoundYield 74%

Procedure

A dry flask is charged with N-(4-chlorobenzyl)-5-iodo-1-methyl-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide (Preparation 40, 0.100 g), cuprous iodide (0.012 g), dichlorobistriphenylphosphine palladium (0.0072 g), propargyl alcohol (0.022 g), and diethylamine (4 mL). The reaction mixture is stirred at room temperature for 5 h and concentrated at reduced pressure. The residue is chromatographed, using 20 g of silica gel packed and eluted with EtOAc/CH2Cl2 (1/1), to obtain the title compound in 74% yield as a tan colored solid. Physical characteristics: M.p. 165-167° C.; 1H NMR (DMSO-d6) δ10.21, 8.67, 8.13, 7.74, 7.38, 5.41, 4.55, 4.35, 3.49, 3.12, 2.85; 13C NMR (DMSO-d6) δ173.69, 162.80, 144.92, 137.79, 133.56, 132.88, 130.54, 128.44, 127.97, 127.49, 126.10, 124.99, 117.98, 109.97, 90.12, 81.73, 48.60, 47.63, 43.24, 40.64, 17.64; MS (ESI+) m/z 422 (M+H)+; HRMS (FAB) m/z 422.1282 (C23H20ClN3O3+H); TLC (silica gel GF): Rf=0.22 acetone/chloroform (1/4).

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue is chromatographed
  3. washeluted with EtOAc/CH2Cl2 (1/1)

Sources & evidence

ORD record
ord-ee7a02d391a445198465738d310d09ef
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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