Triethylamine → HCID 72700164, compound

HRID 710605Notes

Reaction equation

HRID 710605 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[C:10]([C:19]([NH:21][CH:22]3[CH2:24][CH2:23]3)=[O:20])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)#[CH:26].C(N(CC)CC)C>CS(C)=O.[Cu]I>[CH:22]1([NH:21][C:19]([C:10]2[C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[N:14][C:13]=3[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:26]#[C:25][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:3]=3)[N:9]=2)=[O:20])[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 118492322HCID 118492322, compound

Product 1

HCID 72700164HCID 72700164, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To 1-(3-Bromophenyl)-N-cyclopropyl-4-oxo-1,4-dihydropyridino[2,3-c]pyridazine-3-formamide (1 g, 2.6 mmol) in 50 mL DMSO was successively added 3-ethynyl-pyridine (0.34 g, 3.3 mmol), bistriphenylphosphine palladium dichloride (0.53 g, 0.76 mmol), CuI (0.14 g, 0.74 mmol), triethylamine (0.63 g, 6.25 mmol), reacted in a microwave reactor at 100° C. for 90 min. After reaction was complete, extraction was performed with H2O/DCM, and organic phase was purified by preparation chromatography column to obtain product 0.2 g.

Workup

  1. customreacted in a microwave reactor at 100° C. for 90 min
  2. customAfter reaction
  3. extractionextraction
  4. customwas purified by preparation chromatography column

Sources & evidence

ORD record
ord-0ab86d8331964743a5ddbc33bd3c6f06
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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