Water → HCID 86602970, compound

HRID 1180570Notes

Reaction equation

HRID 1180570 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10](Br)[CH:11]=[N:12][CH:13]=3)[N:8]=2)=[O:6])[CH2:3][CH2:2]1.[CH:18]#[CH:19].[C:20](=[O:23])([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Cu]I>[CH:1]1([NH:4][C:5]([C:7]2[C:16]([C:18]#[C:19][CH2:20][OH:23])=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[N:12][CH:13]=3)[N:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 962WaterHCID 6326AcetyleneHCID 11430Potassium CarbonateHCID 69101510HCID 69101510, compound

Product 1

HCID 86602970HCID 86602970, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

8-Bromo-[1,6]naphthyridine-2-carboxylic acid cyclopropylamide, acetylene (2.5 equiv), tetrakis(triphenylphosphine)palladium (0) (5 mol %), copper (I) iodide (25 mol %), and potassium carbonate (3.0 equiv) are dissolved in 5:1 DME:water. The reaction vessel is purged with N2 and stirred overnight at 50° C. The solvent is removed in vacuo and the residue purified by preparative TLC (EtOAc) to afford the desired product as an off-white solid, LC/MS (M+H) 268.2.

Workup

  1. customThe reaction vessel is purged with N2
  2. customThe solvent is removed in vacuo
  3. customthe residue purified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-622a7b6b27e6432c960d4fb16fb21201
Source dataset
uspto-grants-2007_10
Patent number
US07282506B2

Reaction notes

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