HCID 86725300, compound → HCID 71239645, compound

HRID 1403235Notes

Reaction equation

HRID 1403235 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([C:8]2[NH:9][C:10]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](NC)[N:18]=3)=[C:11]([I:16])[C:12]=2[C:13]([NH2:15])=[O:14])[CH:7]=1.[C:26](C1C=CC(N2CCN(C)CC2)=CC=1)#C>C(#N)C.[Cu]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:3]=[CH:4][C:5]([CH3:25])=[C:6]([C:8]2[NH:9][C:10]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:26])[N:18]=3)=[C:11]([I:16])[C:12]=2[C:13]([NH2:15])=[O:14])[CH:7]=1

Participants

6

Reactant 2

HCID 86725300HCID 86725300, compoundHCID 86725301HCID 86725301, compound

Product 1

HCID 71239645HCID 71239645, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

2-(5-Chloro-2-methylphenyl)-4-iodo-5-[2-(methylamino)pyrimidin-4-yl]-1H-pyrrole-3-carboxamide (47 mg, 0.1 mmol) in dry ACN (1 mL) was treated with 1-(4-ethynylphenyl)-4-methylpiperazine (40 mg, 0.2 mmol) and TEA (0.14 mL, 1 mmol). The flask was stirred and purged with nitrogen and then solid CuI (1.0 mg, 0.005 mmol) and Pd(Ph3P)2Cl2 (3.5 mg, 0.005 mmol) were added. The reaction was refluxed for 2 h, then the solvent was evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 95/4/1) to afford the title compound (41 mg, 76%).

Workup

  1. custompurged with nitrogen
  2. temperatureThe reaction was refluxed for 2 h
  3. customthe solvent was evaporated
  4. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 95/4/1)

Sources & evidence

ORD record
ord-37c948da2c454253905d41c631db3b3e
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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