Triethylamine → HCID 68089235, compound

HRID 539777Notes

Reaction equation

HRID 539777 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[F:22])=[N:12][N:11]3[CH:23]=2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[C:27]([Si:29]([CH3:32])([CH3:31])[CH3:30])#[CH:28].C(N(CC)CC)C>C1COCC1.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.[Cu]I>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:23]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:28]#[C:27][Si:29]([CH3:32])([CH3:31])[CH3:30])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=3)[N:9]=2)[N:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67985759HCID 67985759, compound

Product 1

HCID 68089235HCID 68089235, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-(4-bromo-3-nitrophenyl)-6-(2-fluorophenyl)imidazo[1,2-b]pyridazine (0.500 g, 1.21 mmol), ethynyltrimethylsilane (2.42 mmol), PdCl2(PPh3)2(0.0242 mmol) in THF (50 mL) containing triethylamine (6.05 mmol) is added CuI (0.0242 mmol). The mixture is degassed with N2 (5 minutes) then heated at 60° C. for 12 hours. The mixture is filtered, followed by washing with EtOAC, filtrate collected, concentrated under reduced pressure and crude product is purified via chromatography using CH2Cl2 to afford the title compound (0.425 g, 81%) as a yellow solid: Rf 0.56 (CH2Cl2); LCMS (m/z)=431.4 [M+H]+, tR=3.86 min.

Workup

  1. customThe mixture is degassed with N2 (5 minutes)
  2. filtrationThe mixture is filtered
  3. washby washing with EtOAC, filtrate
  4. customcollected
  5. concentrationconcentrated under reduced pressure and crude product
  6. customis purified via chromatography

Sources & evidence

ORD record
ord-3b484bbdf18b4521a68eb9a38b3f0ac2
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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